5-Chloro-o-anisic acid → 5-chloro-N-(5-chlorothiazol-2-yl)-2-methoxybenzamide

HRID 78497

反応式

HRID 78497 の反応式
Cl.[NH2:2][C:3]1[S:4][C:5]([Cl:8])=[CH:6][N:7]=1.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15](O)=[O:16].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15]([NH:2][C:3]1[S:4][C:5]([Cl:8])=[CH:6][N:7]=1)=[O:16]

参加物

6

反応物 3

HCID 769705-Chloro-o-anisic acidHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 866189125-chloro-N-(5-chlorothiazol-2-yl)-2-methoxybenzamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

A mixture of 2-amino-5-chlorothiazole hydrochloric acid (1.0 g, 5.9 mmol), 5-chloro-2-methoxybenzoic acid (1.3 g, 7.0 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (Chem-Impex International, 2.2 g, 12 mmol), 1-hydroxbenzotriazole (0.95 g, 7.0 mmol) and 4-dimethylaminopyridine (0.14 g, 1.2 mmol) in 6 mL of pyridine was allowed to stir at ambient temperature for 72 hours. The reaction mixture was concentrated under reduced pressure and 10 mL of H2O was added. The resulting solids were isolated by filtration, washed with 5 mL of H2O and twice with 5 mL of ethyl acetate, and dried to afford the title compound. MS (DCI/NH3) m/z 303 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure and 10 mL of H2O
  2. additionwas added
  3. customThe resulting solids were isolated by filtration
  4. washwashed with 5 mL of H2O and twice with 5 mL of ethyl acetate
  5. customdried

出典と根拠

ORDレコード
ord-16f7c185f4ca43919749ba8193650962
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

関連ノート

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