Methanol → N-(2-{4-[3-methoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)thiourea

HRID 351276ノート

反応式

HRID 351276 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][NH2:16])=[CH:11][CH:10]=2)[N:6]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:5]=1.[C:27](Cl)(Cl)=[S:28].[OH-].[NH4+:32].CO>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:2][O:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][NH:16][C:27]([NH2:32])=[S:28])=[CH:17][CH:18]=2)[N:6]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:5]=1

参加物

7

反応物 4

HCID 887MethanolHCID 10040ThiophosgeneHCID 14923Ammonium Hydroxide2 回HCID 21090833HCID 21090833、化合物

生成物 1

HCID 21091105N-(2-{4-[3-methoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)thiourea

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a mixture of (2-{4-[3-methoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)amine hydrochloride (150 mg) in CHCl3 (2 ml) and saturated aqueous sodium bicarbonate solution (1 ml) was added thiophosgene (68.8 mg) under ice-bath cooling. The mixture was stirred at ambient temperature for 5 hours. To the mixture was added 28% aqueous ammonium hydroxide (1 ml) and the mixture was stirred at ambient temperature overnight. To the mixture were added 28% aqueous ammonium hydroxide (1 ml) and MeOH (1 ml) and the mixture was stirred at r.t. for 7 hours. The reaction mixture was partitioned between AcOEt and H2O. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was crystallized from ACOEt-IPE. The obtained powder was recrystallized from AcOEt-n-hexane to give N-(2-{4-[3-methoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)thiourea (116 mg) as a powder.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at ambient temperature overnight
  3. stirringthe mixture was stirred at r.t. for 7 hours
  4. customThe reaction mixture was partitioned between AcOEt and H2O
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from ACOEt-IPE
  9. customThe obtained powder was recrystallized from AcOEt-n-hexane

出典と根拠

ORDレコード
ord-7d6984fcc978404284ed06d1ef0f09ce
出典データセット
uspto-grants-2007_02
特許番号
US07183306B2

反応ノート

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