Ethyl isocyanate → N-(6-Methylcyano-1,3-benzothiazol-2-yl)-N'-ethylurea

HRID 9177노트

반응식

HRID 9177 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11]C#N)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:14]([N:16]=[C:17]=[O:18])[CH3:15].[CH2:19]([N:21](CC)CC)C>CN(C)C=O>[CH3:11][C:9]1[CH:8]=[C:7]([C:19]#[N:21])[C:5]2[N:6]=[C:2]([NH:1][C:17]([NH:16][CH2:14][CH3:15])=[O:18])[S:3][C:4]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 21298164(2-Amino-1,3-benzothiazol-6-yl)acetonitrile

생성물 1

HCID 21985550N-(6-Methylcyano-1,3-benzothiazol-2-yl)-N'-ethylurea

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

About 1 g of (2-amino-1,3-benzothiazol-6-yl)methyl cyanide is dissolved in about 10 ml dimethylformamide. About 0.8 ml of ethylisocyanate is added followed by about 1.4 ml triethylamine and the solution is heated to about 80° C. under good agitation. The solution is allowed to stir for about 4–6 hours then cooled to RT. The solvent is removed in vacuo and the solids are washed well with ether. The product is recrystallized from hot EtOAc. 1H NMR 1.09 (t, 3H), 3.1 (m, 2H), 4.1 (s, 2H), 6.72 (m, 1H), 7.32 (m, 1H), 7.61 (d, 1H), 7.85 (s, 1H), 10.7 (s, 1H); LC/MS 2.73 min, 261 (M+1), 259 (M−1).

후처리

  1. temperaturethen cooled to RT
  2. customThe solvent is removed in vacuo
  3. washthe solids are washed well with ether
  4. customThe product is recrystallized from hot EtOAc
  5. customLC/MS 2.73 min, 261 (M+1), 259 (M−1)

출처 및 근거

ORD 기록
ord-157697f4a0e64340ac2d0e8d298b748a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

반응 노트

불러오는 중…