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

HRID 2352465

Reaction equation

HRID 2352465 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 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-d882ecc5046840d9b1721b86a40edac0
Source dataset
uspto-grants-1989_10
Patent number
US04877440

Linked notes

Loading…