Triethylamine → Trifludimoxazin

HRID 405686노트

반응식

HRID 405686 반응식
CNC(NC)=[S:4].C(N(CC)CC)C.[F:14][C:15]1([F:33])[O:20][C:19]2[CH:21]=[C:22]([F:28])[C:23]([N:25]=[C:26]=[O:27])=[CH:24][C:18]=2[N:17]([CH2:29][C:30]#[CH:31])[C:16]1=[O:32].[C:34](N1C=CN=C1)([N:36]1[CH:40]=[CH:39][N:38]=[CH:37]1)=[O:35]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:39][N:38]1[C:37](=[S:4])[N:36]([CH3:40])[C:34](=[O:35])[N:25]([C:23]2[C:22]([F:28])=[CH:21][C:19]3[O:20][C:15]([F:14])([F:33])[C:16](=[O:32])[N:17]([CH2:29][C:30]#[CH:31])[C:18]=3[CH:24]=2)[C:26]1=[O:27]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2723631N,N'-DimethylthioureaHCID 866643002,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

생성물 1

HCID 49831143Trifludimoxazin

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 22728543Water ethylacetate용매

반응 조건

온도
80 °C

실험 절차

To 1,3-dimethylthiourea (2.489 g, 23.89 mmol) and triethylamine (2.78 ml, 19.91 mmol) in dry toluene was added 2,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (5.62 g, 19.91 mmol) in dry toluene. Hereto was subsequently added carbonyldiimidazole (CDI; 6.46 g, 39.8 mmol) and the resulting mixture was stirred at 80° C. overnight. Then the reaction mixture was cooled to room temperature and poured into ethyl acetate/water under stirring. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined extracts were washed with brine, dried with Na2SO4 and concentrated to yield 14.4 g.

후처리

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. stirringunder stirring
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined extracts were washed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customto yield 14.4 g

출처 및 근거

ORD 기록
ord-dad3d3b56d2343c5b9ec6f5b7e1c341f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754008B2

반응 노트

불러오는 중…