Chloroacetyl chloride → N-[5-(4,4-Dimethyl-2,5-dioxo-3-pyridin-4-ylmethyl-imidazolidin-1-yl)-2-trifluoromethoxy-phenyl]-2-chloro-acetamide

HRID 2356933Notes

Reaction equation

HRID 2356933 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[N:15]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[C:14]2=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].CCN(C(C)C)C(C)C.[Cl:38][CH2:39][C:40](Cl)=[O:41]>ClCCCl>[CH3:19][C:16]1([CH3:20])[C:17](=[O:18])[N:13]([C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]([F:10])([F:11])[F:12])=[C:2]([NH:1][C:40](=[O:41])[CH2:39][Cl:38])[CH:3]=2)[C:14](=[O:28])[N:15]1[CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 231103083-(3-Amino-4-trifluoromethoxyphenyl)5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dione

Product 1

HCID 23110283N-[5-(4,4-Dimethyl-2,5-dioxo-3-pyridin-4-ylmethyl-imidazolidin-1-yl)-2-trifluoromethoxy-phenyl]-2-chloro-acetamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

500 mg (1.27 mmol) 3-(3-amino-4-trifluormethoxy-phenyl)-5,5-dimethyl-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione and 172 mg (1.33 mmol) Hünig's base were dissolved in 20 ml 1,2-dichloroethane. The mixture was cooled to −20° C. and treated with a solution of 143 mg (1.27 mmol) chloroacetylchlorid in 15 ml 1,2-dichloroethane. After stirring 1 h at 0° C., 5 ml ethanolic hydrochlric acid were added and the mixture evaporated to dryness. The raw material, containing huening's base hydrochloride was used without further purification.

Workup

  1. customthe mixture evaporated to dryness
  2. additionThe raw material, containing huening's base hydrochloride
  3. customwas used without further purification

Sources & evidence

ORD record
ord-2a8316560dd64ea19eb9406e39344eba
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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