Acetic Anhydride → HCID 20284783, compound

HRID 127527Notes

Reaction equation

HRID 127527 reaction equation
[OH:1][CH:2]([CH:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[S:7][CH2:6][CH2:5]1)[CH3:3].C(OC(=O)C)(=O)C.[OH-].[NH4+]>CS(C)=O>[C:2]([CH:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[S:7][CH2:6][CH2:5]1)(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 202847774-(1-Hydroxyethyl)-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

Product 1

HCID 20284783HCID 20284783, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the product (300 mg) of the above (1) in dimethylsulfoxide (5 ml) is added acetic anhydride (0.7 ml). The mixture is stirred at room temperature for 20 hours. The reaction mixture is poured into ice water, made alkaline with ammonium hydroxide and extracted with ether. The extract is washed with water, dried and evaporated to give an oil (450 mg). The oil is chromatographed on a column of silica gel and eluted with hexane-benzene (3:10) and benzene. The title compound is obtained from the latter eluate. Recrystallization from acetone-petroleum benzine gives colorless needles melting at 120.5°-122.5° C.

Workup

  1. extractionextracted with ether
  2. washThe extract is washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-9be40798e066403b9f9ff29043d75bb6
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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