1,1'-Carbonyldiimidazole → N-(3-methoxy-benzyl)-N-methyl-2-(3,5-dimetoxyphenyl)-2-(phenylsulfanyl)-acetamide

HRID 1666308

Reaction equation

HRID 1666308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:34][NH:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[CH:38]=1>ClCCl>[CH3:44][O:43][C:39]1[CH:38]=[C:37]([CH:42]=[CH:41][CH:40]=1)[CH2:36][N:35]([CH3:34])[C:12](=[O:14])[CH:11]([C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 51522253-Methoxy-N-methylbenzylamineHCID 670817982-(3,5-Dimethoxyphenyl)-2-(phenylsulfanyl)acetic acid

Product 1

HCID 67081986N-(3-methoxy-benzyl)-N-methyl-2-(3,5-dimetoxyphenyl)-2-(phenylsulfanyl)-acetamideYield 105.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(3,5-dimethoxyphenyl)-2-(phenyl-sulfanyl)acetic acid (6.0 g) in dichloromethane (50 ml) was treated with 1,1′-carbonyldiimidazole (3.24 g) at room temperature for 2 hours. A solution of N-methyl-3-methoxy-benzylamine (3.4 g) in dichloromethane (15 ml) was added and the stirring was continued for one hour. The reaction mixture was washed with aqueous hydrochloric acid (1M, 50 ml) and aqueous sodium hydroxide (1M, 50 ml). The organic phase was dried and concentrated to dryness leaving crude N-(3-methoxy-benzyl)-N-methyl-2-(3,5-dimetoxyphenyl)-2-(phenylsulfanyl)-acetamide (9.1 g) as a viscous oil.

Workup

  1. washThe reaction mixture was washed with aqueous hydrochloric acid (1M, 50 ml) and aqueous sodium hydroxide (1M, 50 ml)
  2. customThe organic phase was dried
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-370fd67e1c1a41fba3ad8e657cd42e69
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Linked notes

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