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

HRID 1914638
Notes
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Reaction equation

HRID 1914638 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 27781062-Chloro-5-(trifluoromethyl)benzoyl chlorideHCID 57465891Ethyl 4-amino-2-methylcyclohexane-1-carboxylate

Product 1

HCID 57465893Ethyl 4-(2-chloro-5-(trifluoromethyl)benzamido)-2-methylcyclohexane carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperatureto warm to RT
  2. customthe reaction is quenched with water
  3. custompartitioned between EtOAc and sat. sodium bicarbonate
  4. customThe organic portion is separated
  5. dry with materialdried over MgSO4
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes