Dichloromethane → 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

HRID 348424

反応式

HRID 348424 の反応式
[CH2:1]([C:3]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([C:11]([NH2:13])=[O:12])[NH:5][N:4]=1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH3:20][O:21][CH2:22][CH2:23]Br.C(Cl)Cl>C1COCC1.O>[CH2:1]([C:3]1[N:4]([CH2:23][CH2:22][O:21][CH3:20])[N:5]=[C:6]([C:11]([NH2:13])=[O:12])[C:7]=1[N+:8]([O-:10])=[O:9])[CH3:2]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178438045HCID 178438045、化合物

生成物 1

HCID 112187175-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (2.5 kg, 13.6 Mol), sodium carbonate (1.8 Kg, 17.0 Mol) and 2-bromoethyl methyl ether (1.98 kg, 14.2 Mol) in THF (22.5 L) and water (2.5 L) was heated under reflux and stirred for 20 hours. The mixture was cooled to ambient temperature and CH2Cl2 (67.5 L) and water (22.5 L) were added. The resultant organic and aqueous layers were separated. The aqueous phase was extracted with CH2Cl2 (22.5 L) and the combined organic solution was distilled under atmospheric pressure and replaced with ethyl acetate (33 L) to a final volume of 17 L. The cooled mixture was granulated at ambient temperature for 2 hours, filtered and washed with ethyl acetate (2.5 L). This afforded 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide as a white crystalline solid, 2.10 kg, 57%. m.p.=140° C. Found: C, 44.46; H, 5.79; N, 23.01. C9H14N4O4 requires C, 44.63; H, 5.79; N, 23.14%.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe resultant organic and aqueous layers were separated
  4. extractionThe aqueous phase was extracted with CH2Cl2 (22.5 L)
  5. distillationthe combined organic solution was distilled under atmospheric pressure
  6. waitThe cooled mixture was granulated at ambient temperature for 2 hours
  7. filtrationfiltered
  8. washwashed with ethyl acetate (2.5 L)

出典と根拠

ORDレコード
ord-9587e5b62c124a949c3ffcecd7c14af6
出典データセット
uspto-grants-2007_02
特許番号
US07176311B2

関連ノート

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