Methyl Isocyanate → HCID 20525183, compound

HRID 1702764Notes

Reaction equation

HRID 1702764 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]([OH:20])[CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C1C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]([O:20][C:3](=[O:4])[NH:2][CH3:1])[CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol

Product 1

HCID 20525183HCID 20525183, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 241BenzeneSolvent

Procedure

5.7 g (0.1 mol) of methyl isocyanate and a few drops of dibutyl-tin dilaurate were added to 25.8 g (0.1 mol) of 1-(2,4-dichlorophenyl)-1-hydroxy-2-(imidazol-1-yl)-ethane in 250 ml of benzene, while stirring. The mixture was stirred overnight at 60°-65° C. It was then allowed to cool and the crystalline precipitate was filtered off and rinsed with ether. 25.5 g (81% of theory) of 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)-methylcarbamoyloxy-ethane of melting point 106°-108° C. were obtained.

Workup

  1. stirringThe mixture was stirred overnight at 60°-65° C
  2. temperatureto cool
  3. filtrationthe crystalline precipitate was filtered off
  4. washrinsed with ether

Sources & evidence

ORD record
ord-b1e2566454834229b0b1ba86308b1f8d
Source dataset
uspto-grants-1982_09
Patent number
US04349556

Reaction notes

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