3-Butyn-2-amine, 4-[3-(4-fluorophenoxy)phenyl]-N-hydroxy- → Fenleuton

HRID 861687노트

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HRID 861687 반응식
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:13]#[C:14][CH:15]([NH:17][OH:18])[CH3:16])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.[N-:21]=[C:22]=[O:23].[K+]>C(OCC)(=O)C.O>[OH:18][N:17]([CH:15]([C:14]#[C:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:20][CH:19]=2)[CH:8]=1)[CH3:16])[C:22]([NH2:21])=[O:23]

참가 물질

5

반응물 2

HCID 107545733-Butyn-2-amine, 4-[3-(4-fluorophenoxy)phenyl]-N-hydroxy-HCID 11051572Potassio isocyanate

생성물 1

HCID 72059Fenleuton

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
5 °C

실험 절차

The N-[4-(3-(4-fluorophenoxy)phenyl)-3-butyn-2-yl]hydroxylamine prepared in step 3 above was taken up in ethyl acetate (36 kg) and cooled to 5° C. A solution of freshly prepared potassium isocyanate (10 kg) in water (18 kg) was slowly added and the exotherimic reaction was maintained below 10° C. The reaction mixture was agitated for 30 min. The layers were separated and the organic phase was dried over MgSO4 and filtered. The filtrate was diluted with heptane (58 kg) and agitated for one hour. The resulting crude product was filtered, dissolved in 45° C. ethyl acetate (42 kg). PWA carbon (0.5 kg) and Ultra Norit C (0.5 kg) were added and the mixture was agitated for 30 minutes and filtered. The combined filtrate and washings were diluted with heptane (68 kg) and filtered to provide N-hydroxy-N-[4-(3-(4-fluorophenoxy)phenyl)-3-butyn-2-yl]urea (2.94 kg). m.p. 139°-40° C.; 1H NMR (d6Me2SO) 1.33 (d, 3, J=7 Hz), 5.10 (q, 1, J=7 Hz), 6.55 (s, 2), 6.87 (m, 1), 7.03 (m, 1), 7.13 (m, 3), 7.25 (t, 2, J=8 Hz), 7.37 (t, 1, J=8 Hz), 9.33 (s, 1) ppm; mass spectrum m/e (rel intensity) 332 (80, M+ +NH4), 315 (75, M+ +H), 289 (80), 272 (100). Analysis calculated for C17 H15FN2O3 : C, 64.95, H, 4.81, N, 8.91; found: C, 64.67, H, 4.76, N, 8.81.

후처리

  1. customthe exotherimic reaction
  2. temperaturewas maintained below 10° C
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. additionThe filtrate was diluted with heptane (58 kg)
  7. stirringagitated for one hour
  8. filtrationThe resulting crude product was filtered
  9. dissolutiondissolved in 45° C. ethyl acetate (42 kg)
  10. additionPWA carbon (0.5 kg) and Ultra Norit C (0.5 kg) were added
  11. stirringthe mixture was agitated for 30 minutes
  12. filtrationfiltered
  13. additionThe combined filtrate and washings were diluted with heptane (68 kg)
  14. filtrationfiltered

출처 및 근거

ORD 기록
ord-d1f728fddee74a5e93347735ec28da9a
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714633

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