Methanol → HCID 54397444, compound

HRID 1939284Notes

Reaction equation

HRID 1939284 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])=[O:12])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.O.[CH3:29]O>>[CH3:29][O:2][C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])=[O:12])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 9836770HCID 9836770, compound

Product 1

HCID 54397444HCID 54397444, compound

Procedure

N-(3-carboxyphenyl)-N'-(2-methoxy-5-chlorophenyl) urea (3.00 g, 9.4 mmol) was suspended in methanol (100 ml). Concentrated sulfuric acid (1.0 ml) was added and the reaction was heated at reflux for 6 hours. The reaction mixture was poured into cold (0° C.) water (600 ml). Filtration of the suspension afforded the crude product. The crude product was purified by column chromatography on silica using dichloromethane/ethyl acetate 19:1 as eluent. 2.35 g of the title compound was isolated.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 6 hours
  3. filtrationFiltration of the suspension
  4. customafforded the crude product
  5. customThe crude product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-5a6e9c31d7bf466998d5dd078663eb97
Source dataset
uspto-grants-1997_12
Patent number
US05696138

Reaction notes

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