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

HRID 1024429ノート

反応式

HRID 1024429 の反応式
[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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53404682Ethyl 5-(4-nitrophenyl)thiazole-2-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d63e61d66f8f4924865d6cea9ab620ae
出典データセット
uspto-grants-2014_05
特許番号
US08722901B2

反応ノート

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