Benzoyl isocyanate → N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide

HRID 471470

반응식

HRID 471470 반응식
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[C:11]([N:19]=[C:20]=[O:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCOCC1>[C:7]([C:6]1[C:5]([CH3:9])=[C:4]([CH3:10])[S:3][C:2]=1[NH:1][C:20]([NH:19][C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:21])#[N:8]

참가 물질

4

반응물 2

HCID 78210Benzoyl isocyanateHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

생성물 1

HCID 57456902N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide수율 90.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 2-amino-4,5-dimethylthiophene-3-carbonitrile (example 4b) (25 g, 164.5 mmol) in 1,4-dioxane (600 mL) was added benzoyl isocyanate (24.2 g, 164.5 mmol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The precipitate was collected by filtration, washed with 1,4-dioxane (20 mL×3), and dried under vacuum at 40° C. for 3 hours to give N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide (44.35 g, 90%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 2.10 (s, 3H), 2.24 (s, 3H), 7.52-7.56 (m, 2H), 7.64-7.69 (m, 1H), 8.01-8.03 (m, 2H), 11.57 (brs, 1H), 12.05 (brs, 1H). MS 300 (MH+).

후처리

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with 1,4-dioxane (20 mL×3)
  3. customdried under vacuum at 40° C. for 3 hours

출처 및 근거

ORD 기록
ord-a6c8c70a47744978b9f09400eaa28380
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633186B2

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