Diethyl Ether → 1-(2-Chloro4,5-difluorobenzoyl)-3-(2-methoxy-5-nitrophenyl)urea

HRID 887892Notes

Reaction equation

HRID 887892 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5].[Cl:13][C:14]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:15]=1[C:16]([N:18]=[C:19]=[O:20])=[O:17].C(OCC)C>CN1CCCC1=O>[Cl:13][C:14]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:15]=1[C:16]([NH:18][C:19]([NH:5][C:4]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])=[O:20])=[O:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 74472-Methoxy-5-nitroanilineHCID 115575832-Chloro-4,5-difluorobenzoyl Isocyanate

Product 1

HCID 116681521-(2-Chloro4,5-difluorobenzoyl)-3-(2-methoxy-5-nitrophenyl)ureaYield 79%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4.0 g (23.8 mmol) of 2-methoxy-5-nitroaniline were dissolved in 10 ml of N-methyl-2-pyrrolidinone, and 5.2 g (23.8 mmol) of 2-chloro-4,5-difluorobenzoyl isocyanate were added. Slight warming occurred. After 15 minutes at room temperature, diethyl ether was added, and the resulting precipitate was filtered off with suction. 6.6 g (79%) of the desired product were obtained.

Workup

  1. temperatureSlight warming
  2. filtrationthe resulting precipitate was filtered off with suction

Sources & evidence

ORD record
ord-e72eac6b62c34bb68ed3ed23452198ea
Source dataset
uspto-grants-2012_08
Patent number
US08247452B2

Reaction notes

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