ChemicalBook CAS DataBase List N-(tert-butyl)-4-methylbenzamide

N-(tert-butyl)-4-methylbenzamide synthesis

15synthesis methods

Product Name:N-(tert-butyl)-4-methylbenzamide
CAS Number:42498-32-8
Molecular formula:C12H17NO
Molecular Weight:191.27

104-87-0 Synthesis

104-87-0
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$6.00/25g

75-65-0 Synthesis

75-65-0
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$10.00/10ml

42498-32-8
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$80.00/100mg

Yield:42498-32-8 98%

Reaction Conditions:

Stage #1: 4-methyl-benzaldehydewith sodium azide;trifluorormethanesulfonic acid;acetic acid at 40; for 2 h;Schmidt Reaction;
Stage #2: tert-butyl alcoholwith trifluorormethanesulfonic acid at 40; for 2 h;Ritter Amidation;

Steps:

General experimental procedure for the synthesis Amides 4

General procedure: To a magnetically stirred solution of benzaldehyde (1 mmol) and NaN₃ (1.5 mmol) in AcOH (0.2 mL), TfOH (2 mmol) was added and the reaction mixture was heated at 40 °C for 1-2 h. On the complete conversion of aldehyde (monitored by TLC), alcohol (1 mmol) was added along with TfOH (1 mmol). The reaction was continued to heating at 90 °C (in the case of t-butanol the reaction temperature was 40 °C) for another 3-5 h. After the completion, the reaction was cooled to 0 °C and saturated aq NaHCO₃ was added slowly. The precipitate formed was filtered and washed with plenty of cold water and dried to obtain the desired secondary benzamide as white solid in 98% yield. (Compounds obtained were pure hence, no further purification or recrystallisation was required).

References:

Singh, Garima;Dada, Ravikrishna;Yaragorla, Srinivasarao [Tetrahedron Letters,2016,vol. 57,# 39,p. 4424 - 4427] Location in patent:supporting information