Tetrahydrofuran → 7-Chloro-5-(2-chlorophenyl)-1,3-dihydro-2 H-1,4-benzodiazepin-2-ylidenepropanedioic acid diethyl ester

HRID 1156237ノート

反応式

HRID 1156237 の反応式
C([C:3]([CH2:10][CH3:11])([C:7]([O-:9])=[O:8])[C:4]([O-:6])=[O:5])C.[H-].[Na+].P(Cl)(OCC)(O[CH2:17][CH3:18])=O.[Cl:23][C:24]1[CH:25]=[CH:26][C:27]2[NH:33]C(=O)C[N:30]=[C:29]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[Cl:41])[C:28]=2[CH:42]=1.[CH2:43]1COC[CH2:44]1>>[CH2:17]([O:9][C:7](=[O:8])[C:3](=[C:10]1[CH2:11][N:30]=[C:29]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:41])[C:28]2[CH:42]=[C:24]([Cl:23])[CH:25]=[CH:26][C:27]=2[NH:33]1)[C:4]([O:6][CH2:43][CH3:44])=[O:5])[CH3:18]

参加物

6

反応物 5

HCID 8028Tetrahydrofuran2 回HCID 13139Diethyl chlorophosphateHCID 17925DelorazepamHCID 24758Sodium hydrideHCID 69515632,2-Diethylpropanedioate

生成物 1

HCID 705450437-Chloro-5-(2-chlorophenyl)-1,3-dihydro-2 H-1,4-benzodiazepin-2-ylidenepropanedioic acid diethyl ester

実験手順

Diethylmalonate (45.55 ml) was added to THF (200 ml). The mixture was maintained at room temperature with a wet ice bath while sodium hydride (14 g of a 60% oil dispersion) was added portionwise over 1 hr. To the resulting suspension, diethyl chlorophosphate (14.45 ml) was added dropwise over 50 minutes. After a 30 minute agitation cycle, a THF solution of 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (15.25 g) was added dropwise over 20 minutes. The resulting solution was allowed to agitate for 1 hr. The pH was adjusted from 5.0 to 5.5, and the reaction solution was concentrated (40° C./30 mm) to remove the THF. To the residue was added cold water (600 ml) and hexane (100 ml). The crystalline solid obtained was filtered and washed with cold water and hexane. After the solid was dried to constant weight, the end product was obtained.

後処理

  1. additionwas added portionwise over 1 hr
  2. concentrationthe reaction solution was concentrated (40° C./30 mm)
  3. customto remove the THF
  4. additionTo the residue was added cold water (600 ml) and hexane (100 ml)
  5. customThe crystalline solid obtained
  6. filtrationwas filtered
  7. washwashed with cold water and hexane
  8. customAfter the solid was dried to constant weight
  9. customthe end product was obtained

出典と根拠

ORDレコード
ord-2d2e9ee03ae74048a907f17b911ecfec
出典データセット
uspto-grants-1982_06
特許番号
US04335042

反応ノート

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