Phenyl thioxochloroformate → HCID 19434000, compound

HRID 1735999Notes

Reaction equation

HRID 1735999 reaction equation
[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:6][CH:5](O)[C:4]=2[CH:3]=1.C1C=CC(OC(Cl)=S)=CC=1>CN(C)C1C=CN=CC=1.ClCCCl>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:11])(=[O:12])[N:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 19434001HCID 19434001, compound

Product 1

HCID 19434000HCID 19434000, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of the product from Step C (1.4 g, 4.05 mmol) and 4-dimethylaminopyridine (0.74 g, 6.08 mmol) in 1,2-dichloroethane (10 mL) were cooled in an ice bath. Phenyl chlorothionoformate (0.67 mL, 4.86 mM) was added slowly. The cooling bath was removed and the mixture was stirred at room temperature for 18 hr, mixed with 3:1 hexane/ethyl acetate (25 mL) and filtered through silica gel. The filtrate was concentrated and heated under vacuum (200° C./0.5 mm Hg) approximately 5 min followed by cooling the mixture to room temperature. The residue was purified by column chromatography (silica gel, 3:1 hexane/ethyl acetate to 7:3 methylene chloride/methanol) which gave 0.91 g (65%) of the desired product as an oil which was not purified further.

Workup

  1. customThe cooling bath was removed
  2. additionmixed with 3:1 hexane/ethyl acetate (25 mL)
  3. filtrationfiltered through silica gel
  4. concentrationThe filtrate was concentrated
  5. temperatureheated under vacuum (200° C./0.5 mm Hg) approximately 5 min
  6. temperatureby cooling the mixture to room temperature
  7. customThe residue was purified by column chromatography (silica gel, 3:1 hexane/ethyl acetate to 7:3 methylene chloride/methanol) which

Sources & evidence

ORD record
ord-b4ef2a722857442d90e68bf378ab2bf3
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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