Sodium Hydroxide → 1-(2-Chloro-4,5-difluorobenzoyl)-3-(5-amino-2-methoxyphenyl)urea

HRID 349730Notes

Reaction equation

HRID 349730 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:3]=1[C:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=1[O:19][CH3:20])=[O:8])=[O:5].[OH-].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:3]=1[C:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=1[O:19][CH3:20])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 116681521-(2-Chloro4,5-difluorobenzoyl)-3-(2-methoxy-5-nitrophenyl)urea

Product 1

HCID 115665791-(2-Chloro-4,5-difluorobenzoyl)-3-(5-amino-2-methoxyphenyl)urea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2.2 g (5.7 mmol) of 1-(2-chloro-4,5-difluorobenzoyl)-3-(2-methoxy-5-nitrophenyl)urea were heated to the boiling temperature in 50 ml of ethyl acetate and admixed with 6.4 g (28.5 mmol) of SnCl2 monohydrate. After 1 hour, the mixture was allowed to cool to room temperature and the pH was adjusted to 8 using 2 N sodium hydroxide solution. The precipitate which formed was filtered off and washed with methanol, and the mother liquor was washed twice with H2O, dried and concentrated under reduced pressure. The resulting product (1.4 g) was reacted in step d without further purification.

Workup

  1. customThe precipitate which formed
  2. filtrationwas filtered off
  3. washwashed with methanol
  4. washthe mother liquor was washed twice with H2O
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting product (1.4 g) was reacted in step d without further purification

Sources & evidence

ORD record
ord-1fb4996461a449f38ad9d49c6b43dfa6
Source dataset
uspto-grants-2007_02
Patent number
US07179941B2

Reaction notes

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