Water → 1-(4-Chloro-3-(trifluoromethyl)phenyl)-3-hydroxyurea

HRID 2094792Notes

Reaction equation

HRID 2094792 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[O:10]CC)=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].Cl.[OH:19][NH2:20].O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:20][OH:19])=[O:10])=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15]

Participants

5

Reactant 3

HCID 962WaterHCID 140397Ethyl 4-chloro-3-trifluoromethylcarbanilateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 252211521-(4-Chloro-3-(trifluoromethyl)phenyl)-3-hydroxyureaYield 71.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 4-chloro-3-(trifluoromethyl)phenylcarbamate (10 g, 0.0373 mol) and hydroxyl amine hydrochloride (13 g, 0.1868 mol) were refluxed in acetic acid for 12 hours and the organic layer was evaporated under vacuum to get oil. This oil was mixed with water (100 ml) and the obtained precipitate was stirred at room temperature for 1-2 hours. The obtained solid was filtered and washed thoroughly with water. The wet cake was vacuum dried at 50° C. to afford 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-hydroxyurea (6.8 g) as a white crystalline solid.

Workup

  1. customthe organic layer was evaporated under vacuum
  2. customto get oil
  3. filtrationThe obtained solid was filtered
  4. washwashed thoroughly with water
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-3b8a6f5f811d4d62984d49dba8c788d1
Source dataset
uspto-grants-2013_05
Patent number
US08445687B2

Reaction notes

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