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

HRID 9103

반응식

HRID 9103 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14].C(N(CC)CC)C>CN(C)C=O>[C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:16]([NH:15][CH2:13][CH3:14])=[O:17])[S:3][C:4]=2[CH:10]=1)#[N:12]

참가 물질

5

반응물 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 43271392-Aminobenzothiazole-6-carbonitrile

생성물 1

HCID 21985533N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-ethylurea

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

2-Amino-1,3-benzothiazole-6-carbonitrile (0.2 g) was dissolved in about 5 mL dimethylformamide. About 0.2 mL of ethylisocyanate was added, followed by about 0.3 mL triethylamine and the solution was heated to about 80° C. under good agitation. The solution was allowed to stir for about 4 hours then cooled to room temperature. The solvent was removed in vacuo and the solids were washed well with ether. The product was further purified by column chromatography and after drying in vacuo, about 0.14 grams was isolated. 1H NMR 1.1 (t, 3H, J=7.2 Hz), 3.2 (m, 2H), 6.8 (s, 1H), 7.7 (m, 2H), 8.4 (s, 1H), 11.0 (s, 1H), LC/MS 2.54 min, 247 (MH+), 245 (M−H−), lab RP-HPLC RT 7.8 minutes.

후처리

  1. temperaturethen cooled to room temperature
  2. customThe solvent was removed in vacuo
  3. washthe solids were washed well with ether
  4. customThe product was further purified by column chromatography
  5. customafter drying in vacuo
  6. customabout 0.14 grams was isolated
  7. custom1H NMR 1.1 (t, 3H, J=7.2 Hz), 3.2 (m, 2H), 6.8 (s, 1H), 7.7 (m, 2H), 8.4 (s, 1H), 11.0 (s, 1H), LC/MS 2.54 min, 247 (MH+), 245 (M−H−), lab RP-HPLC RT 7.8 minutes

출처 및 근거

ORD 기록
ord-4bb201544c5043cd978fe2b16f5062ab
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

연결된 노트

불러오는 중…