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Triphosgene → 1-(2-Chloro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea

HRID 1505179
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HRID 1505179 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].ClC(Cl)(O[C:18](=[O:24])[O:19][C:20](Cl)(Cl)Cl)Cl.[N-:26]=[C:27]=[O:28]>CCOC(C)=O.CN(C=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][C:27]([NH:26][C:3]1[C:4]2[NH:5][C:18](=[O:24])[O:19][C:20]=2[CH:8]=[CH:9][CH:2]=1)=[O:28]
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참가 물질

6

반응물 3

HCID 94429TriphosgeneHCID 105034IsocyanateHCID 22337564(2-Chloro-4-(trifluoromethyl)phenyl)methanamine

생성물 1

HCID 534761351-(2-Chloro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea수율 10%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매
2회

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온도
80 °C

실험 절차

Commercially available 2-chloro-4-trifluoromethylbenzylamine (572 mg, 2.7 mmol) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (809 mg, 2.7 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1b (270 mg, 1.8 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 70 mg of a white solid. Yield=10% 1HNMR (DMSO, 400 MHz) δ 4.45 (2H, d, J=6 Hz), 6.97 (2H, d, J=4.4 Hz), 7.07 (2H, m), 7.63 (1H, d, J=8 Hz), 7.74 (2H, d), 7.86 (1H, s), 8.61 (1H, bs), 10.90 (1H, bs); [M+1] 386.6 (C16H11ClF3N3O3 requires 385.7).

후처리

  1. additionwas added to the solution
  2. customthen evaporated
  3. dissolutiondissolved in 5 ml of DMF
  4. temperaturethe mixture was warmed at 80° C. for 8 hours
  5. customThe solvent was evaporated
  6. dissolutionthe crude was dissolved in AcOEt (30 ml)
  7. washwashed with water (1×20 ml) and brine
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe purification of the crude residue by chromatographic column

출처 및 근거

ORD 기록
ord-92127f4280de4b9e8d94527f1121aa83
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09216975B2

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