Acetic Acid → HCID 53870822, compound

HRID 2308939Notes

Reaction equation

HRID 2308939 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][C:8](=[CH:11][N:12](C)C)[C:7](=[O:15])[C:6]=2[CH:16]=1.[C:17]([O:21][C:22]([N:24]([CH3:26])N)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(O)(=O)C>CO.O1CCCC1>[C:17]([O:21][C:22]([N:24]([CH3:26])[NH:12][CH:11]=[C:8]1[C:7](=[O:15])[C:6]2[CH:16]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[S:10][CH2:9]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 37482801-Boc-1-methylhydrazineHCID 38135366-chloro-2,3-dihydro-3-dimethylaminomethylene-4H-1-benzothiopyran-4-one

Product 1

HCID 53870822HCID 53870822, compoundYield 129.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-chloro-2,3-dihydro-3-dimethylaminomethylene-4H-1-benzothiopyran-4-one (34.13 g), 1-t-butoxycarbonyl-1-methylhydrazine (59.14 g), and acetic acid (23.14 ml) in methanol (2 l) and tetrahydrofuran (1 l) was stirred at ambient temperature for 6 hours and then evaporated in vacuo. To the residue was added aqueous sodium bicarbonate and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo to give 3-(2-t-butoxycarbonyl-2-methylhydrazinomethylene)-6-chloro-2,3-dihydro-4H-1-benzothiopyran-4-one (61.65 g).

Workup

  1. customevaporated in vacuo
  2. additionTo the residue was added aqueous sodium bicarbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ad84993324b04b359da9ebb6f3715884
Source dataset
uspto-grants-1987_09
Patent number
US04692444

Reaction notes

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