Dichloromethane → HCID 178459584, compound

HRID 1769797Notes

Reaction equation

HRID 1769797 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[C:8]([O-:11])(=[S:10])[CH3:9].[CH2:12](Cl)Cl>CN(C)C1C=CN=CC=1>[C:8]([OH:11])(=[S:10])[CH3:9].[CH2:5]([O:4][C:1](=[O:3])[CH2:2][CH2:8][SH:10])[CH:6]=[CH2:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 178476994HCID 178476994, compound

Product 1

HCID 178459584HCID 178459584, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The reaction mixture from step 1 was cooled under nitrogen and then diluted with 200 g. of methylene chloride. Then, 289 g. of acetic anhydride, along with a catalyst of 0.5 g. of 4-dimethylaminopyridine, were added to the reaction mixture. The reaction mixture was stirred for 1 hour at which time NMR analysis of a vacuum stripped aliquot indicated complete conversion to the desired thioacetate. The product was distilled at 132°-134° C. at 20 mm Hg to yield 355 g. of product (80%).

Workup

  1. additiondiluted with 200 g
  2. distillationThe product was distilled at 132°-134° C. at 20 mm Hg
  3. customto yield 355 g

Sources & evidence

ORD record
ord-0c5fe30b838a44fca544c8ef5a4bbc05
Source dataset
uspto-grants-1995_01
Patent number
US05382640

Reaction notes

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