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

HRID 1252352

반응식

HRID 1252352 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-c05cdcf7574e4c4cb07a343f8ed48be9
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04743290

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