Hydrogen Sulfide → HCID 22003635, compound

HRID 324449

Reaction equation

HRID 324449 reaction equation
[SH2:1].CC(C)([O-])C.[K+].[CH2:8]([C:10]1O[C:12]2[CH2:19][CH2:18][C:17]3[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:16]=3[C:15](=[O:25])[C:13]=2[N:14]=1)[CH3:9]>CN(C)C=O>[CH2:8]([C:10]1[S:1][C:12]2[CH2:19][CH2:18][C:17]3[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:16]=3[C:15](=[O:25])[C:13]=2[N:14]=1)[CH3:9]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 220036422-Ethyl-9,10-dihydro-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22003635HCID 22003635, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydrogen sulphide was passed through a suspension of potassium tert-butoxide (9.31 g) in N,N-dimethylformamide (80 ml) at 5° C. until the mixture was saturated. The product from example 1 step (v) (5.0 g) was added and the reaction mixture stirred at room temperature for 2 h. The mixture was poured onto ice, acidified to pH3 and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 40-50% ethyl acetate in isohexane.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with 40-50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-f10df7e12b0b47ecb0ea620d43f44c2e
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

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