Methyl 3-(aminosulfonyl)-2-thiophenecarboxylate → 2-(Hydroxymethyl)thiophene-3-sulfonamide

HRID 1252352

Reaction equation

HRID 1252352 reaction equation
[NH2:1][S:2]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10](OC)=[O:11])(=[O:4])=[O:3].[BH4-].[Li+]>O1CCCC1>[OH:11][CH2:10][C:6]1[S:7][CH:8]=[CH:9][C:5]=1[S:2]([NH2:1])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 101012Methyl 3-(aminosulfonyl)-2-thiophenecarboxylateHCID 4148881Lithium borohydride

Product 1

HCID 142549372-(Hydroxymethyl)thiophene-3-sulfonamideYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5.0 g of methyl 3-aminosulfonylthiophene-2-carboxylate in 200 mL of tetrahydrofuran was added 0.75 g of lithium borohydride. After heating at reflux for two hours the reaction was quenched with water and acidified with concentrated hydrochloric acid. The desired product was then extracted into methylene chloride which was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 1.8 g of a yellow solid, m.p. 85°-89°.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for two hours the reaction
  3. customwas quenched with water
  4. extractionThe desired product was then extracted into methylene chloride which
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c05cdcf7574e4c4cb07a343f8ed48be9
Source dataset
uspto-grants-1988_05
Patent number
US04743290

Linked notes

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