5-Chloro-2,4-dimethoxyaniline → trans-N-(5-Chloro-2,4-dimethoxyphenyl)-2,2-dimethyl-3-phenylcyclopropanecarboxamide

HRID 2174604Notes

Reaction equation

HRID 2174604 reaction equation
[CH3:1][C:2]1([CH3:14])[C@@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@@H:3]1[C:11]([OH:13])=O.[Cl:15][C:16]1[C:17]([O:25][CH3:26])=[CH:18][C:19]([O:23][CH3:24])=[C:20]([CH:22]=1)[NH2:21]>>[Cl:15][C:16]1[C:17]([O:25][CH3:26])=[CH:18][C:19]([O:23][CH3:24])=[C:20]([NH:21][C:11]([C@H:3]2[C@H:4]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:2]2([CH3:1])[CH3:14])=[O:13])[CH:22]=1

Participants

3

Reactant 2

HCID 668075-Chloro-2,4-dimethoxyanilineHCID 68582304(1S,3S)-2,2-dimethyl-3-phenylcyclopropane-1-carboxylic acid

Product 1

HCID 86709737trans-N-(5-Chloro-2,4-dimethoxyphenyl)-2,2-dimethyl-3-phenylcyclopropanecarboxamideYield 66%

Procedure

2,2-Dimethyl-trans-3-phenylcyclopropanecarboxylic acid (500 mg, 2.63 mmol) and 5-chloro-2,4-dimethoxyaniline (493 mg, 2.63 mmol) were reacted as described under General Procedure D to furnish the title compound (620 mg, 66%) as a beige solid. 1H NMR (300 MHz, CDCl3) δ 8.49 (s, 1H), 7.78 (s, 1H), 7.30-7.19 (m, 5H), 6.53 (s, 1H), 3.94 (s, 3H), 3.89 (s, 3H), 2.83 (d, J=5.7 Hz, 1H), 1.86 (d, J=5.7 Hz, 1H), 1.42 (s, 3H), 0.97 (s, 3H). mp 160-162° C. ESIMS m/z [M+H]+ 360.2.

Sources & evidence

ORD record
ord-0ffd546820ba4e48b15e9d7fb0677669
Source dataset
uspto-grants-2015_06
Patent number
US09062013B2

Reaction notes

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