Acetic Acid → HCID 57663930, compound

HRID 1510257Notes

Reaction equation

HRID 1510257 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:11])[C:4]1[S:5][CH:6]=[CH:7][CH:8]=1.C(O)(=O)C.[Cl:29]N1C(=O)CCC1=O>ClCCl>[Cl:29][C:6]1[S:5][C:4]([C@H:3]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)=[O:11])[CH2:2][OH:1])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 57663905HCID 57663905, compound

Product 1

HCID 57663930HCID 57663930, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[(1R)-2-hydroxy-1-(2-thienyl)ethyl]-3-[4-(4-pyridinyl)phenyl]urea (700 mg) and acetic acid (734 mg) in dichloromethane (10 mL) were added N-chlorosuccinimide (303 mg) and the mixture was refluxed for 3 hours. The mixture was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with chloroform/methanol (9:1) and crystallized from ethanol to afford 1-[(1R)-1-(5-chloro-2-thienyl)-2-hydroxyethyl]-3-[4-(4-pyridinyl)phenyl]urea (280 mg) as a crystal.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by column chromatography on silica gel eluting with chloroform/methanol (9:1)
  4. customcrystallized from ethanol

Sources & evidence

ORD record
ord-7475e78936a443368c8b338bc87b9e73
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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