Sodium Hydroxide → Methyl 4-(4-(4-aminophenyl)(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate

HRID 2298619노트

반응식

HRID 2298619 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:15]3[CH:16]=[C:17]([C:21]([O:23][CH3:24])=[S:22])[S:18][C:19]=3[CH3:20])[S:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+]>O1CCCC1.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:15]3[CH:16]=[C:17]([C:21]([O:23][CH3:24])=[S:22])[S:18][C:19]=3[CH3:20])[S:13][CH:14]=2)=[CH:6][CH:5]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 86758673Methyl 4-(4-(4-nitrophenyl)(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate

생성물 1

HCID 86583820Methyl 4-(4-(4-aminophenyl)(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate수율 72.2%

시약·촉매·용매 2

HCID 160960Diamminetetrachlorotitanate(IV)촉매HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 4-(4-(4-nitrophenyl)(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate (800 mg, 2 mmol) was dissolved in 150 mL tetrahydrofuran and treated with 20% titanium chloride solution (Fisher Scientific, Pittsburgh, Pa., USA) for 1 h. The mixture was poured into 2 M sodium hydroxide solution (100 mL), extracted with dichloromethane (4×50 mL). The combined organic layers were washed with saturated brine solution and dried over anhydrous sodium sulfate. The solid was filtered off, and the solvent removed in vacuo. This material was purified by column chromatography on silica gel (30 g) eluting with dichloromethane:methanol 98/2 (v:v) to give methyl 4-(4-(4-aminophenyl)(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate (500 mg, 69%) as a solid. 1H-NMR (DMSO-d6; 300 MHz) δ8.17 (s, 1H), 7.77 (s, 1H), 7.74 and 6.62 (AB quartet, 2H, J=8.6 Hz), 5.35 (s, 2H), 3.86 (s, 3H), 2.74 (s, 3H). ). Mass spectrum (MALDI-TOF, CHCA matrix, m/z): Calcd. for C16H14N2O2S3 363.0 (M+H), found 362.4.

후처리

  1. extractionextracted with dichloromethane (4×50 mL)
  2. washThe combined organic layers were washed with saturated brine solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe solid was filtered off
  5. customthe solvent removed in vacuo
  6. customThis material was purified by column chromatography on silica gel (30 g)
  7. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-22a7ba07a67a4956aaa43d005da11dfe
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492403B1

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