Phenyl thioxochloroformate → HCID 19426779, compound

HRID 863588Notes

Reaction equation

HRID 863588 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:24]=[C:23]([CH3:25])[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH:15]([C:17]3[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=3)[OH:16])=[C:9]([CH3:26])[CH:8]=2)=[N:3]1.Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[S:29]>C(#N)C.CN(C1C=CN=CC=1)C>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:8]=[C:9]([CH3:26])[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH:15]([C:17]3[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=3)[O:16][C:28]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[S:29])=[C:23]([CH3:25])[CH:24]=2)=[N:3]1

Participants

5

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 22103401HCID 22103401, compound

Product 1

HCID 19426779HCID 19426779, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-[4-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-1-hydroxy-butyl]-1-methylimidazole (690 mg, 1.94 mmol) in 30 ml of acetonitrile was added at 20° C. 473 mg (3.88 mmol) of DMAP and 403 mg (2.33 mmol) of phenyl chlorothioformate, and the mixture was stirred at 20° C. for 3 h. The solvent was concentrated in vacuo and the residue was partitioned between methylene chloride and an aqueous sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (20 cm column, ethyl acetate/hexane, 1/1-4/1) to afford 750 mg (78%) of 2-[4-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-1-phenoxythiocarbonyloxy-butyl]-1-methylimidazole, as a yellow oil.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe residue was partitioned between methylene chloride
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (20 cm column, ethyl acetate/hexane, 1/1-4/1)

Sources & evidence

ORD record
ord-0699e6c9e443477a9526197def2d51db
Source dataset
uspto-grants-1998_02
Patent number
US05721261

Reaction notes

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