Phenyl thioxochloroformate → HCID 54310283, compound

HRID 1457036Notes

Reaction equation

HRID 1457036 reaction equation
[OH:1][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([C:19]3[N:20]=[N:21][N:22]([CH3:24])[N:23]=3)=[CH:14][C:13]=2[CH3:25])[N:6]=[CH:5][N:4]=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[S:28]>C(#N)C.CN(C1C=CN=CC=1)C>[O:29]([C:27]([O:1][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[C:13]([CH3:25])=[CH:14][C:15]([C:19]3[N:20]=[N:21][N:22]([CH3:24])[N:23]=3)=[CH:16][C:17]=2[CH3:18])[N:6]=[CH:5][N:4]=1)=[S:28])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 70498Phenyl thioxochloroformate2×HCID 22103452HCID 22103452, compound

Product 1

HCID 54310283HCID 54310283, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of 5-hydroxymethyl-1-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethyl-phenoxy]-propyl]-1,2,4-triazole (343 mg, 1 mmol) in 15 ml of acetonitrile was added DMAP (244 mg, 2 mmol) and phenyl chlorothioformate (381 mg, 2.2 mmol). The mixture was stirred at 20° C. for 7 h. An additional phenyl chlorothioformate (1 equiv) was added, and the mixture was stirred for 15 h. The solvent was removed in vacuo and 5-phenoxythiocarbonyloxymethyl-1-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole was isolated and used without further purification.

Workup

  1. stirringthe mixture was stirred for 15 h
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-92519c27c56346268776b5ddeea74b8e
Source dataset
uspto-grants-1998_12
Patent number
US05846986

Reaction notes

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