Hydrochloric Acid → 7-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol4-one

HRID 324417

Reaction equation

HRID 324417 reaction equation
CC(C)([O-])C.[K+].[SH2:7].[CH2:8]([C:10]1[CH:11]=[CH:12][C:13]2[C:23](=[O:24])[C:18]3[N:19]=[C:20]([CH3:22])O[C:17]=3[CH2:16][CH2:15][C:14]=2[CH:25]=1)[CH3:9].Cl>CN(C)C=O>[CH2:8]([C:10]1[CH:11]=[CH:12][C:13]2[C:23](=[O:24])[C:18]3[N:19]=[C:20]([CH3:22])[S:7][C:17]=3[CH2:16][CH2:15][C:14]=2[CH:25]=1)[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 402Hydrogen SulfideHCID 220035847-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 220036117-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of potassium tert-butoxide (1.80 g) in dry N,N-dimethylformamide (20 ml) was cooled to 5° C. and saturated with hydrogen sulphide. The product from example 3 step (vi) (1.00 g) was added and the reaction stirred at room temperature for 1 hour. The mixture was poured into ice, acidified to pH4 with 2N hydrochloric acid and extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4) and evaporated to give an orange solid which was purified by chromatography eluting with 50% ethyl acetate in isohexane.

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give an orange solid which
  7. customwas purified by chromatography
  8. washeluting with 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-adbaab83bb094bc6ab27259c64182025
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

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