Tert-Butylamine → N-tert-butyl-3-(chloromethyl)benzamide

HRID 1878321Notes

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].C(N(C(C)C)C(C)C)C>ClCCl>[C:12]([NH:16][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([CH2:2][Cl:1])[CH:4]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: -15 °C

Procedure

3-(Chloromethyl)benzoyl chloride (2.26 ml, 15.9 mmol) was added to a stirred solution of dichloromethane (50 mL) at −30° C. (cold-bath temperature) under argon. After 10 minutes stirring, a solution of tert-butylamine (1.66 mL, 15.9 mmol) and N-ethyl-N-isopropylpropan-2-amine (5.53 mL, 31.7 mmol) in dichloromethane (5 mL) was added dropwise. Stirring was continued while allowing the cold-bath temperature to slowly increase to −15° C. over 45 minutes. The reaction mixture was concentrated under vacuum to give the intermediate N-tert-butyl-3-(chloromethyl)benzamide as a white solid.

Workup

stirringStirring
concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-0cca54cd88504531975d1bc23d600d16
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314091B2

Reaction notes

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