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

HRID 861687ノート

反応式

HRID 861687 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 72059Fenleuton

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d1f728fddee74a5e93347735ec28da9a
出典データセット
uspto-grants-1998_02
特許番号
US05714633

反応ノート

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