Phenyl thioxochloroformate → HCID 19434002, compound

HRID 1735991Notes

Reaction equation

HRID 1735991 reaction equation
O[CH:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])[S:10][C:6]=2[S:5](=[O:20])(=[O:19])[N:4]([CH2:21][CH2:22][O:23][CH3:24])[CH2:3]1.C1C=CC(OC(Cl)=S)=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:24][O:23][CH2:22][CH2:21][N:4]1[CH:3]=[CH:2][C:7]2[CH:8]=[C:9]([S:11]([NH:14][C:15]([CH3:16])([CH3:18])[CH3:17])(=[O:12])=[O:13])[S:10][C:6]=2[S:5]1(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 19434009HCID 19434009, compound

Product 1

HCID 19434002HCID 19434002, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The product from Step G (4.11 g, 10.31 mmol) and 4-dimethylaminopyridine (2.52 g, 20.6 mmol) were combined in dichloromethane (50 mL) and the mixture was cooled by means of an ice bath. Phenyl chlorothionoformate (2.1 mL, 15.5 mmol) was added rapidly to the mixture and the cooling bath removed. After three hours the mixture was washed with 2N HCl (15 mL), water (15 mL), saturated aqueous sodium chloride (20 mL), dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, hexane/ethyl acetate) to provide the desired product (2.14 g, 39%) as an oil. This oil was heated under vacuum (200° C./5 mm Hg) for approximately 5 minutes (until no more condensate collected) and then purified by column chromatography (silica, hexane/ethyl acetate) to provide the desired product (1.48 g, 97%) which was used in the next step.

Workup

  1. temperaturethe mixture was cooled by means of an ice bath
  2. customthe cooling bath removed
  3. washAfter three hours the mixture was washed with 2N HCl (15 mL), water (15 mL), saturated aqueous sodium chloride (20 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a residue which
  6. customwas purified by column chromatography (silica, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-976a2e563ad94c3da60bafbcfea64c22
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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