Chloroacetyl chloride → 2-chloro-N-(2,4-dimethoxybenzyl)-N-[2-(3-fluorobenzoyl)-4-methoxyphenyl]acetamide

HRID 1169692Notes

Reaction equation

HRID 1169692 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)=[O:16].C(N(CC)CC)C.[Cl:37][CH2:38][C:39](Cl)=[O:40]>ClCCl>[Cl:37][CH2:38][C:39]([N:6]([CH2:5][C:4]1[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:3]=1[O:2][CH3:1])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[C:15](=[O:16])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)=[O:40]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 8471TriethylamineHCID 68659721{2-[(2,4-Dimethoxybenzyl)amino]-5-methoxyphenyl}(3-fluorophenyl)methanone

Product 1

HCID 687184392-chloro-N-(2,4-dimethoxybenzyl)-N-[2-(3-fluorobenzoyl)-4-methoxyphenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of {2-[(2,4-dimethoxybenzyl)amino]-5-methoxyphenyl}(3-fluorophenyl)methanone (190 mg, 0.480 mmol) in 5 mL of dichloromethane was added triethylamine (0.335 mL, 2.40 mmol), followed by chloroacetyl chloride (0.115 mL, 1.44 mmol). After 30 minutes, another portion of chloroacetyl chloride (0.115 mL, 1.44 mmol) was added, and the mixture was stirred overnight. The reaction was partitioned between EtOAc and saturated NaHCO3 solution, and the organic layer was washed with saturated NH4Cl solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The titled product was isolated as a brown foam (229 mg, 100% yield) which was used in the next step without further purification ESI+MS: 472.1 [M+H]+.

Workup

  1. customThe reaction was partitioned between EtOAc and saturated NaHCO3 solution
  2. washthe organic layer was washed with saturated NH4Cl solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ba4aafbf2dc4f87970b509822760c37
Source dataset
uspto-grants-2010_11
Patent number
US07825131B2

Reaction notes

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