2-Chloro-5-(trifluoromethyl)benzoyl chloride → Ethyl 4-(2-chloro-5-(trifluoromethyl)benzamido)-2-methylcyclohexane carboxylate

HRID 1914638Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]([CH3:13])[CH2:3]1.[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:16]=1[C:17](Cl)=[O:18]>C1COCC1>[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][C:16]=1[C:17]([NH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]([CH3:13])[CH2:3]1)=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 4-amino-2-methylcyclohexanecarboxylate (780 mg, 4.21 mmol) in THF (10 ml) is treated with TEA (1.174 ml, 8.42 mmol) and the reaction mixture is cooled to 0° C. 2-Chloro-5-(trifluoromethyl)benzoyl chloride (921 mg, 3.79 mmol) is added dropwise and the reaction mixture is stirred and allowed to warm to RT. After 3 hours, the reaction is quenched with water and partitioned between EtOAc and sat. sodium bicarbonate. The organic portion is separated and dried over MgSO4 and concentrated in vacuo to afford the title compound which is used without further purification. [MH]+392.26.

Workup

temperatureto warm to RT
customthe reaction is quenched with water
custompartitioned between EtOAc and sat. sodium bicarbonate
customThe organic portion is separated
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-70adbd8794814d348469f2dffe36bccb
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614213B2

Reaction notes

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