Lithium borohydride → 5-Hydroxymethyl-thiophene-2-sulfonic acid amide

HRID 2425055Notes

Reaction equation

HRID 2425055 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([S:10](=[O:13])(=[O:12])[NH2:11])=[CH:8][CH:9]=1)=O.[BH4-].[Li+]>O1CCCC1>[OH:2][CH2:3][C:5]1[S:6][C:7]([S:10]([NH2:11])(=[O:13])=[O:12])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydride2×HCID 13425727Methyl 5-sulfamoylthiophene-2-carboxylate

Product 1

HCID 657442385-Hydroxymethyl-thiophene-2-sulfonic acid amideYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.442 g 5-sulfamoyl-thiophene-2-carboxylic acid methyl ester in 8 ml tetrahydrofuran was added 0.044 g lithiumborohydride and the mixture was stirred at room temperature for 20 h. To the resulting mixture was added an other 0.088 g lithiumborohydride and the mixture was stirred at room temperature for 2 h and at reflux for 20 h. The resulting suspension was partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel with ethyl acetate to yield 0.300 g of the title compound as white crystals melting at 70-71° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. temperatureat reflux for 20 h
  3. customThe resulting suspension was partitioned between water and ethyl acetate
  4. customThe phases were separated
  5. customthe organic phase was purified by chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-30f95fef1d514bff80a04d3ff3bb65d9
Source dataset
uspto-grants-2011_06
Patent number
US07964633B2

Reaction notes

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