Hydrochloric Acid → HCID 13911635, compound

HRID 653447Notes

Reaction equation

HRID 653447 reaction equation
[O:1]=[C:2]1[CH2:14][CH2:13][C:5]2[S:6][C:7]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:8][C:4]=2[CH2:3]1.[BH4-].[Na+].O.Cl>C(O)C>[OH:1][CH:2]1[CH2:14][CH2:13][C:5]2[S:6][C:7]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:8][C:4]=2[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 13911634HCID 13911634, compound

Product 1

HCID 13911635HCID 13911635, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 5-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-2-sulfonamide (1.0 g, 0.0043 mole) in ethanol (30 ml) was added sodium borohydride (160 mg, 0.004 mole). The suspended solid dissolved within 10 minutes in a slightly exothermic reaction. Stirring was continued overnight at room temperature. After dilution with water (15 ml), the ethanol was stripped in vacuo. The residual aqueous solution was cooled in an ice bath and acidified with 6N HCl. The precipitate was collected, washed with water, and dried to yield 0.7 g (70%) of product as an off-white crystalline solid, mp 176°-179° C.

Workup

  1. dissolutionThe suspended solid dissolved within 10 minutes in a slightly exothermic reaction
  2. temperatureThe residual aqueous solution was cooled in an ice bath
  3. customThe precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-bb70093df9ef482281186573e8ab9291
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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