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

HRID 857716노트

반응식

HRID 857716 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4378230f23de4082ad5559dd767b7bbd
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144899B2

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