Benzoyl isocyanate → N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide

HRID 711762노트

반응식

HRID 711762 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH3:11])[C:3]=1[C:4]#[N:5].[C:12]([N:20]=[C:21]=[O:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCOCC1>[C:4]([C:3]1[C:6]([NH:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][C:21]([NH:20][C:12](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:22])#[N:5]

참가 물질

4

반응물 2

HCID 78210Benzoyl isocyanateHCID 127157172-Amino-6-(methylamino)benzonitrile

생성물 1

HCID 67401506N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide수율 20%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 2-amino-6-(methylamino)benzonitrile (example 156b) (0.14 g, 0.97 mmol) in 1,4-dioxane (3 mL) was added benzoyl isocyanate (0.17 g, 1.17 mmol). The reaction mixture was stirred at room temperature under nitrogen overnight. The obtained precipitate was filtered and dried under vacuum to give N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide (57 mg, 20%). 1H NMR (400 MHz, DMSO-d6) δ 2.75 (d, J=4.4 Hz, 3H), 6.26 (d, J=4.8 Hz, NH), 6.43 (d, J=9.6 Hz, 1H), 7.40-7.43 (m, 2H), 7.51-7.55 (m, 2H), 7.63-7.65 (m, 1H), 8.01 (d, J=8.4 Hz, 2H), 11.23 (s, NH), 11.30 (s, NH). MS 295 (MH+).

후처리

  1. filtrationThe obtained precipitate was filtered
  2. customdried under vacuum

출처 및 근거

ORD 기록
ord-1116b7ab27b146efb1b9d93ac602cf91
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181276B2

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