Ethanol → HCID 15885622, compound

HRID 1936866Notes

Reaction equation

HRID 1936866 reaction equation
Br[CH:2]1[CH2:17][CH2:16][C:5]2=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:7][C:8]([S:9][CH3:10])=[C:4]2[C:3]1=O.[C:19]([NH2:27])(=[S:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)C>C(OCC)(=O)C.O1CCCC1>[CH3:10][S:9][C:8]1[O:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[C:4]=1[C:3]1[N:27]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:26][C:2]=1[CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 702EthanolHCID 683563ThiobenzamideHCID 18388329HCID 18388329, compound

Product 1

HCID 15885622HCID 15885622, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

A mixture of ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]furan-1-carboxylate (2.60 g), thiobenzamide (2.14 g) and ethanol (60 ml) was refluxed under heating for 5 hours, after which it was diluted with ethyl acetate-tetrahydrofuran (3:1, v/v, 400 ml), washed with water and dried (MgSO4), after which the solvent was distilled off to yield ethyl 4,5-dihydro-8-methylthio-2-phenylfuro[3,4-e]benzothiazole-6-carboxylate (1.67 g, 57.6%), which was then recrystallized from ethyl acetate-hexane. Colorless needles. Melting point 170-171° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 5 hours
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-14d2c935314f4ad3ba244d77088d2c67
Source dataset
uspto-grants-2002_05
Patent number
US06391905B1

Reaction notes

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