Hydrazine hydrate (1:1) → HCID 20096580、化合物

HRID 2221110ノート

反応式

HRID 2221110 の反応式
[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2C(=O)C3=CC=CC=C3C2=O)=[CH:8][C:7]=1[N+:23]([O-:25])=[O:24])[CH3:2].O.NN>COCCOC>[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[N+:23]([O-:25])=[O:24])[CH3:2]

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 20096586HCID 20096586、化合物

生成物 1

HCID 20096580HCID 20096580、化合物収率 91.3%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

1,2-Dimethoxyethane (1.0 L) is added to (2-nitro4-phtalimido-phenyl)-carbamic acid ethyl ester (101 g, 0.28 mol) and the mixture is heated under reflux. Hydrazine monohydrate (19.6 g, 0.39 mol) is added dropwise over 10 minutes and the mixture is stirred at reflux for 1.5 hours. Upon cooling to ambient temperature the mixture is filtered and the solids are washed with dimethoxyethane (250 mL) on the filter. The filtrate is concentrated by means of evaporation and the red crystalline product is recrystallized from toluene (350 mL), precipitated product is filtered off and dried in vacuo. The mother liquor is concentrated to half the original volume and left standing for 16 hours. Precipitated material is filtered off and recrystallized as before. The recrystallized solids are combined to furnish a total of 57.6 g (90%) dark red title compound. LC/MS (m/z) 225.1 (MH+); tR=2.08 min. 1H NMR (CDCl3): 1.33 (t, 3H); 3.77 (s, 2H, NH2); 4.23 (q, 2H); 6.98 (dd, 1H); 7.45 (d, 1H); 8.28 (d, 1H); 9.39 (s, 1H, NH).

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. temperatureat reflux for 1.5 hours
  4. filtrationis filtered
  5. washthe solids are washed with dimethoxyethane (250 mL) on the filter
  6. concentrationThe filtrate is concentrated by means of evaporation
  7. customthe red crystalline product is recrystallized from toluene (350 mL)
  8. customprecipitated product
  9. filtrationis filtered off
  10. customdried in vacuo
  11. concentrationThe mother liquor is concentrated to half the original volume
  12. waitleft
  13. filtrationPrecipitated material is filtered off
  14. customrecrystallized as before

出典と根拠

ORDレコード
ord-a51d9804279f43c594fe32c28cb5dc6c
出典データセット
uspto-grants-2008_05
特許番号
US07368472B2

反応ノート

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