Triethylamine → 3-chloro-4-fluoro-N-(1-methyl-1-phenylethyl)benzamide

HRID 21239

Reaction equation

HRID 21239 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](Cl)=[O:6].[C:12]([NH2:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])[CH3:13].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([NH:21][C:12]([CH3:14])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13])=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68509CumylamineHCID 27365483-Chloro-4-fluorobenzoyl Chloride

Product 1

HCID 684919423-chloro-4-fluoro-N-(1-methyl-1-phenylethyl)benzamideYield 97.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 16, 3-chloro-4-fluorobenzoyl chloride (3.00 g, 15.5 mmol) was dissolved in dichloromethane (60 mL), and the solution was treated with cumylamine (2.45 mL, 17.1 mmol), triethylamine (3.24 mL, 23.3 mmol) and DMAP (189 mg, 1.05 mmol), followed by purification by slurry using diisopropylether to obtain 3-chloro-4-fluoro-N-(1-methyl-1-phenylethyl)benzamide (4.39 g, yield 97%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-ffb7690b8cdc47748458e2379a0e394f
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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