Acetic Acid → HCID 70544650, compound

HRID 1156235Notes

Reaction equation

HRID 1156235 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: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][CH:36]=3)[C:28]=2[CH:41]=1.[C:42](O)(=O)[CH3:43]>C1COCC1>[CH2:17]([O:9][C:7](=[O:8])[C:3](=[C:10]1[CH2:11][N:30]=[C:29]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:28]2[CH:41]=[C:24]([Cl:23])[CH:25]=[CH:26][C:27]=2[NH:33]1)[C:4]([O:6][CH2:42][CH3:43])=[O:5])[CH3:18]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 2997NordiazepamHCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 69515632,2-Diethylpropanedioate

Product 1

HCID 70544650HCID 70544650, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethylmalonate (45.55 ml) was added to tetrahydrofuran (200 ml). The mixture was maintained at room temperature while sodium hydride (16 g of a 60% oil dispersion) was added 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-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (13.54 g) was added dropwise over 20 minutes. The resulting solution was allowed to agitate for 1 hr. The pH was adjusted with acetic acid from 5.0 to 5.5, and the reaction solution was concentrated under vacuum (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 water and hexane. After the solid was dried, the end product was obtained.

Workup

  1. additionwas added over 1 hr
  2. concentrationthe reaction solution was concentrated under vacuum (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 water and hexane
  8. customAfter the solid was dried
  9. customthe end product was obtained

Sources & evidence

ORD record
ord-03bbc15cb7d9485f8756ea064bd058dd
Source dataset
uspto-grants-1982_06
Patent number
US04335042

Reaction notes

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