Hydrochloric Acid → 5-(4-Nitrophenyl)thiazole-2-carboxylic acid

HRID 1024429

반응식

HRID 1024429 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]([C:15]([O:17]CC)=[O:16])=[N:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Cl>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:14][C:13]([C:15]([OH:17])=[O:16])=[N:12][CH:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53404682Ethyl 5-(4-nitrophenyl)thiazole-2-carboxylate2회

생성물 1

HCID 671503095-(4-Nitrophenyl)thiazole-2-carboxylic acid수율 76.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl 5-(4-nitrophenyl)thiazole-2-carboxylate (Intermediate 2, step A, 3.6 g) was dissolved in THF (90 ml). 1 Molar aqueous NaOH (52 ml) was added and stirred at RT for 15-20 minutes. The reaction mixture was acidified with 1M HCl, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to get pale yellow colored solid. Solid was crystallized in EtOAc/Pet ether to yield 2.48 g (76%) of the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 14.21 (bs, 1H), 8.7 (s, 1H), 8.31 (d, 2H), 8.1 (d, 2H); MS (ES+): m/z 251 (M+1).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get pale yellow colored solid
  6. customSolid was crystallized in EtOAc/Pet ether

출처 및 근거

ORD 기록
ord-d63e61d66f8f4924865d6cea9ab620ae
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722901B2

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