Acetic-formic anhydride → HCID 13536744, compound

HRID 464758Notes

Reaction equation

HRID 464758 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([CH3:16])([CH3:15])[S:12][C:11]=2[CH:17]=1)=[O:6])=[N+]=[N-].[CH:18]([O-])=[O:19].[Na+].C(OC(=O)C)=O>C(O)=O>[CH:18]([NH:1][CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([CH3:16])([CH3:15])[S:12][C:11]=2[CH:17]=1)=[O:6])=[O:19]

Participants

5

Reactant 3

HCID 75269Acetic-formic anhydrideHCID 2723810Sodium FormateHCID 13536743HCID 13536743, compound

Product 1

HCID 13536744HCID 13536744, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

10 g of 5-azidoacetyl-2,2-dimethyl-1,3-benzoxathiole (VIII) was added portionwise to a cooled solution of 20 g stannous chloride and 7 g sodium formate in the mixture of 16 ml of acetic-formic anhydride and 9 ml of formic acid. After 14 hours at room temperature the mixture was quenched with ice and dilute hydrochloric acid and extracted with ethyl acetate. The extract was dried over MgSO4, evaporated, and the residue purified by chromatography through a column of silica gel eluted with ethyl acetate-hexane (1:1) to yield 6 g of 5-formamidoacetyl-2,2-dimethyl-1,3-benzoxathiole (IX) as a yellow oil.

Workup

  1. customAfter 14 hours at room temperature the mixture was quenched with ice and dilute hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over MgSO4
  4. customevaporated
  5. customthe residue purified by chromatography through a column of silica gel
  6. washeluted with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-3c610817406e44599c350c0c6eeeed72
Source dataset
uspto-grants-1985_10
Patent number
US04548951

Reaction notes

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