Sodium Hydroxide → N-(2-Chloro-6-Methylphenyl)-N'-(1,4,5,6-Tetrahydropyrimidin-2-yl)urea Monohydrochloride Hemihydrate

HRID 358345ノート

反応式

HRID 358345 の反応式
[ClH:1].[NH2:2][C:3]1[NH:4][CH2:5][CH2:6][CH2:7][N:8]=1.[OH-].[Na+].[O-:11]S([O-])(=O)=O.[Na+].[Na+].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[N:26]=[C:27]=[O:28]>C1COCC1>[OH2:11].[ClH:18].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[NH:26][C:27]([NH:2][C:3]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]=1)=[O:28].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[NH:26][C:27]([NH:2][C:3]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]=1)=[O:28].[ClH:1]

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 2681232-Chloro-6-methylphenyl isocyanateHCID 225575271,3-Diazinan-2-imine hydrochloride

生成物 1

HCID 70484368N-(2-Chloro-6-Methylphenyl)-N'-(1,4,5,6-Tetrahydropyrimidin-2-yl)urea Monohydrochloride Hemihydrate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 8.14 g (0.060 mol) of 2-amino-1,4,5,6-tetrahydropyrimidine hydrochloride, 6.0 g (0.075 mol) of 50% NaOH and 75 ml of THF was stirred for 0.5 hours at room temperature and then 15 g Na2SO4 was added. After stirring for 0.5 hours, a solution of 6.70 g (0.040 mol) of 2-chloro-6-methylphenyl isocyanate in 50 ml of THF was added over a period of 0.5 hours. After stirring for 1 hour, the reaction mixture was filtered, the filtrate evaporated in vacuo and the residue dissolved in 25 ml of 10% HCl and 25 ml of H2O with warming. After filtration through diatomaceous earth chilling in ice gave the crystalline hydrochloride which was recrystallized from cold H2O after treatment with charcoal affording 7.15 g (59%). This material was dried in vacuo (20° C., 5 mm Hg) to constant weight to give 7.11 g (59%) of pure N-(2-chloro-6-methylphenyl)-N'-(1,4,5,6-tetrahydropyrimidin-2-yl)urea monohydrochloride hemihydrate, m.p. (190) 215°-220° C. melts, then forms a new solid; m.p. 243°-245° C.; IR(CHCl3) 3224, 1713, 1677, 1641, 1543 cm-1 ; UV max. (MeOH) 236 (16,200) and 217 nm infl (21,500).

後処理

  1. stirringAfter stirring for 0.5 hours
  2. stirringAfter stirring for 1 hour
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate evaporated in vacuo
  5. dissolutionthe residue dissolved in 25 ml of 10% HCl
  6. temperature25 ml of H2O with warming
  7. filtrationAfter filtration through diatomaceous earth
  8. temperaturechilling in ice

出典と根拠

ORDレコード
ord-29b23d9ac2394b69b67560da70ac2e11
出典データセット
uspto-grants-1984_08
特許番号
US04466966

反応ノート

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