Ammonium Chloride → 5-Chloro-2-(1H-tetrazol-1-YL)benzamide

HRID 857716ノート

反応式

HRID 857716 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].[Cl-].[NH4+].Cl.C[N:20](C)CCCN=C=NCC.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[C:6]([CH:10]=1)[C:7]([NH2:20])=[O:8]

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117155615-Chloro-2-(1H-tetrazol-1-yl)benzoic acid

生成物 1

HCID 218661695-Chloro-2-(1H-tetrazol-1-YL)benzamide収率 115.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 5-chloro-2-(1H-tetraazol-1-yl)benzoic acid (2.0 g, 8.9 mmol), ammonium chloride (0.95 g, 17.8 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.4 g, 17.8 mmol), HOAt (2.4 g, 17.8 mmol) and DIEA (6.2 mL, 35.6 mmol) in DMF (26 mL) was stirred at room temperature overnight. Water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine. Drying and solvent evaporation gave 5-chloro-2-(1H-tetrazol-1-yl)benzamide (2.3 g); 1H NMR (400 MHz, CD3OD): δ 9.44 (s, 1H), 7.82 (d, J=2.3 Hz, 1H), 7.75 (dd, J=2.3, 8.5 Hz, 1H), 7.66 (d, J=8.5 Hz, 1H).

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customDrying
  4. customsolvent evaporation

出典と根拠

ORDレコード
ord-4378230f23de4082ad5559dd767b7bbd
出典データセット
uspto-grants-2006_12
特許番号
US07144899B2

反応ノート

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