N-methyl-2-pyrrolidone → 1-(2-Chloro-4,5-difluorobenzoyl)-3-(5-amino-2-methoxyphenyl)urea

HRID 887893Notes

Reaction equation

HRID 887893 reaction equation
O.[Sn](Cl)Cl.[Cl:5][C:6]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:7]=1[C:8]([NH:10][C:11]([NH:13][C:14]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:15]=1[O:23][CH3:24])=[O:12])=[O:9].CN1CCCC1=O>C(OCC)(=O)C.CO>[NH2:20][C:18]1[CH:17]=[CH:16][C:15]([O:23][CH3:24])=[C:14]([NH:13][C:11]([NH:10][C:8](=[O:9])[C:7]2[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:6]=2[Cl:5])=[O:12])[CH:19]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 116681521-(2-Chloro4,5-difluorobenzoyl)-3-(2-methoxy-5-nitrophenyl)ureaHCID 43835034Tin dichloride dihydrate

Product 1

HCID 115665791-(2-Chloro-4,5-difluorobenzoyl)-3-(5-amino-2-methoxyphenyl)ureaYield 67%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

5.8 g (25.9 mmol) of tin dichloride hydrate were added to 2.0 g (5.2 mmol) of 1-(2-chloro-4,5-difluorobenzoyl)-3-(2-methoxy-5-nitrophenyl)urea in 20 ml of ethyl acetate/methanol mixture at 70° C. After 1 hour, 30 ml of N-methyl-2-pyrrolidinone were added, and the mixture was stirred for a further 2 hours. After cooling, the reaction mixture was made basic and the resulting precipitate was filtered off with suction. The phases were separated. The organic phase was then washed three times with water, dried and concentrated under high vacuum. 1.2 g (67%) of the desired product were obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was filtered off with suction
  3. customThe phases were separated
  4. washThe organic phase was then washed three times with water
  5. customdried
  6. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-b620a01271774162a39ac485a129fc22
Source dataset
uspto-grants-2012_08
Patent number
US08247452B2

Reaction notes

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