Water → HCID 23347797, compound

HRID 1855718Notes

Reaction equation

HRID 1855718 reaction equation
[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([CH2:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1.[BH4-].[Na+].O>C(O)C>[OH:1][CH:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([CH2:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23347793HCID 23347793, compound

Product 1

HCID 23347797HCID 23347797, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Twenty-seven g (0.129 M) of 4,5,6,7-Tetrahydro-7-oxobenzo[b]thien-4-ylacetamide is dissolved in absolute ethanol (270 ml) and treated with sodium borohydride (4.9 g, 0.129 M). The mixture is stirred at room temperature overnight, water (250 ml) is added and stirring continued for 2 hours. The bulk of the ethanol is evaporated and the precipitated solid is filtered off, washed twice with water (total 50 ml) and air dried to afford the title compound (13.73 g, 50.4% yield) as an off white solid, m.p. 175° C. to 179° C. dec.

Workup

  1. stirringstirring
  2. waitcontinued for 2 hours
  3. customThe bulk of the ethanol is evaporated
  4. filtrationthe precipitated solid is filtered off
  5. washwashed twice with water (total 50 ml) and air
  6. customdried

Sources & evidence

ORD record
ord-ea7084097dd1420e814a8216a3cfe854
Source dataset
uspto-grants-1980_08
Patent number
US04216149

Reaction notes

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