Tetrahydrofuran → HCID 70543283, compound

HRID 1156238Notes

Reaction equation

HRID 1156238 reaction equation
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:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[N:31]=CC(=O)[N:34]=[C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=12.[CH2:45]1COC[CH2:46]1>>[CH2:17]([O:9][C:7](=[O:8])[C:3](=[C:10]1[CH2:11][N:31]=[C:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[Cl:23])[C:36]2[CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=[CH:40][C:35]=2[NH:34]1)[C:4]([O:6][CH2:45][CH3:46])=[O:5])[CH3:18]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 69515632,2-DiethylpropanedioateHCID 20535592HCID 20535592, compound

Product 1

HCID 70543283HCID 70543283, compound

Procedure

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 (16 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 5-(2-chlorophenyl)-7-nitro-2H-1,4-benzodiazepin-2-one (15.8 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 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.

Workup

  1. additionwas added portionwise over 1 hr
  2. concentrationthe reaction 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

Sources & evidence

ORD record
ord-3d76c371a75742e2a32022ef24273994
Source dataset
uspto-grants-1982_06
Patent number
US04335042

Reaction notes

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