Carbon Dioxide → Diazepam

HRID 1658936Notes

Reaction equation

HRID 1658936 reaction equation
[OH-].[K+].[CH:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:16]3[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=3[NH:14][C:12](=[O:13])[CH:11](C([O-])=O)[N:10]=2)=[CH:7][CH:8]=1.O[K].[K+].S(OC)(O[CH3:32])(=O)=O.C(OC(C)C)(C)C.C(=O)=O>CCOCC.C(O)(=O)C.O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]2[N:14]([CH3:32])[C:12](=[O:13])[CH2:11][N:10]=[C:9]([C:6]3[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=3)[C:16]=2[CH:17]=1

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 6497Dimethyl SulfateHCID 7914Diisopropyl EtherHCID 14797Potassium HydroxideHCID 178524857HCID 178524857, compound

Product 1

HCID 3016DiazepamYield 80%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

An aqueous solution prepared by dissolving 7 g. of potassium hydroxide in 15 ml. of water is added to an aqueous solution of 3 g. of compound 4306 CB, then 1.8 g. of dimethyl sulphate is gradually added (about 5 minutes) with stirring, care being taken that the temperature does not rise above 25°C. After the addition is ended, the mixture is left for 2 hours at room temperature, then acidified with acetic acid. A pasty product separates which is covered with diisopropyl ether, and the suspension thus formed is heated to boiling for a few minutes; evolution of carbon dioxide takes place. The product is cooled, diluted with ether and the aqueous phase is separated. Upon evaporation of the solvent, there is obtained a residue which is crystallized from diisopropyl ether. Yield: 80%; m.p. 132°C. The product is identical with the product obtained according to Example 16.

Workup

  1. customAn aqueous solution prepared
  2. dissolutionby dissolving 7 g
  3. customdoes not rise above 25°C
  4. additionAfter the addition
  5. customthe suspension thus formed
  6. temperatureis heated
  7. waitto boiling for a few minutes
  8. temperatureThe product is cooled
  9. customthe aqueous phase is separated
  10. customUpon evaporation of the solvent
  11. customthere is obtained a residue which
  12. customis crystallized from diisopropyl ether
  13. customobtained

Sources & evidence

ORD record
ord-ce53a1b1f95e4bcab996090f5f14d580
Source dataset
uspto-grants-1976_06
Patent number
US03966793

Reaction notes

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