Hydrochloric Acid → 4-methyl-N-[4-(4-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

HRID 619041노트

반응식

HRID 619041 반응식
Br.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl>N1C=CC=CC=1>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:16][C:13]2[S:14][CH:15]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=3)[N:12]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 124305704-(4-nitrophenyl)thiazol-2(3H)-imine hydrobromide

생성물 1

HCID 100450034-methyl-N-[4-(4-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide수율 16.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 0.5 g of 4-(4-nitro-phenyl)-thiazol-2-ylamine hydrobromide with 0.35 g of p-toluenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid and the mixture was extracted three times with 100 ml of ethyl acetate each time. The organic phases were combined, dried with magnesium sulphate and the solvent was removed on a rotary evaporator. The residue was chromatographed on 60 g of Kieselgel 60 with diethyl ether/ethyl acetate (1:1) as the eluent. The product-containing fractions were concentrated and the residue was digested with a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution. The product separated upon neutralization of the filtrate with concentrated hydrochloric acid. Recrystallization from 50 ml of 60% ethanol yielded 0.10 g of 4-methyl-N-[4-(4-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as yellowish crystals.

후처리

  1. extractionthe mixture was extracted three times with 100 ml of ethyl acetate each time
  2. dry with materialdried with magnesium sulphate
  3. customthe solvent was removed on a rotary evaporator
  4. customThe residue was chromatographed on 60 g of Kieselgel 60 with diethyl ether/ethyl acetate (1:1) as the eluent
  5. concentrationThe product-containing fractions were concentrated
  6. additionthe residue was digested with a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  7. customThe product separated upon neutralization of the filtrate with concentrated hydrochloric acid
  8. customRecrystallization from 50 ml of 60% ethanol

출처 및 근거

ORD 기록
ord-504b7dc40c6545ef91dac4d2537ae340
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958910

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