Dimethyl Sulfoxide → Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate

HRID 1433134Notes

Reaction equation

HRID 1433134 reaction equation
CS(C)=O.C[O:6][C:7]1[CH:16]=[C:15]2[C:10](C(Cl)=CC=N2)=[CH:9][C:8]=1C(N)=O.[Cl:21][C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:23]=1[NH:29][C:30](NC1CC1)=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+]>O>[Cl:21][C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:23]=1[NH:29][C:30](=[O:31])[O:6][C:7]1[CH:16]=[CH:15][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 229364184-Chloro-7-methoxyquinoline-6-carboxamideHCID 23135084ME-92

Product 1

HCID 11277058Phenyl N-(2-chloro-4-hydroxyphenyl)carbamateYield 142.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To dimethyl sulfoxide (20 mL) were added 7-methoxy-4-chloroquinoline-6-carboxamide (0.983 g), 1-(2-chloro-4-hydroxyphenyl)-3-cyclopropylurea (1.13 g) and cesium carbonate (2.71 g), and the mixture was heated and stirred at 70° C. for 23 hours. The reaction mixture was cooled to room temperature, and water (50 mL) was added, and the resultant crystals were then filtered off to give 1.56 g of the titled compound (yield: 88%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe resultant crystals were then filtered off

Sources & evidence

ORD record
ord-db89dc6381f8450598a79e6ac2611704
Source dataset
uspto-grants-2009_11
Patent number
US07612208B2

Reaction notes

Loading…