Tetrahydrofuran → HCID 57901642, compound

HRID 1851435Notes

Reaction equation

HRID 1851435 reaction equation
[O:1]=[C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[NH:15][S:16]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)(=[O:18])=[O:17])[C:6]=2[CH2:5][CH2:4][CH2:3]1.O1CCCC1.[BH4-].[Na+]>CO>[OH:1][CH:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[NH:15][S:16]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)(=[O:18])=[O:17])[C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 57901829HCID 57901829, compound

Product 1

HCID 57901642HCID 57901642, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of N-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-8-yl)thiophene-2-sulfonamide (0.50 g), tetrahydrofuran (20 mL) and methanol (2 mL) was added sodium borohydride (0.11 g) at 0° C., and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the resulting crystals were filtrated, washed with water, and dried to give the title compound (0.43 g, yield 86%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point>175° C. (decomposition).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition10% aqueous citric acid solution was added
  3. filtrationthe resulting crystals were filtrated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-16002db62fcf47b4bfe3630883341824
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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