Hexamethylphosphoramide → HCID 22749545, compound

HRID 1763253Notes

Reaction equation

HRID 1763253 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:19])=[N:13][C:14]([C:15]([O:17]C)=O)=[C:10]3[CH2:9][C:8](=[O:20])[N:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:6]=2[CH:27]=1.[Cl-].[Li+].[CH3:30][N:31]([CH3:40])P(=O)(N(C)C)N(C)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:19])=[N:13][C:14]([C:15]([N:31]([CH3:40])[CH3:30])=[O:17])=[C:10]3[CH2:9][C:8](=[O:20])[N:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:6]=2[CH:27]=1

Participants

4

Reactant 3

HCID 12679HexamethylphosphoramideHCID 433294Lithium ChlorideHCID 22749547HCID 22749547, compound

Product 1

HCID 22749545HCID 22749545, compound

Procedure

A mixture of 1.2 g of methyl 8-chloro-4,6-dihydro-1-methyl-6-phenyl-5-oxo-5H-imidazo[1,5-a][1,5]benzodiazepin-3-carboxylate, 2 g of lithium chloride and 12 ml of hexamethyl phosphoric triamide was stirred and heated up to 230°. As soon as this temperature was reached, the reaction mixture was cooled and partitioned between methylene chloride and water. The organic phase was washed with water, dried over sodium sulfate and evaporated. Crystallization of the residue from ether yielded the end product which was recrystallized from ethyl acetate/hexane for analysis, mp 213°-215°.

Workup

  1. temperatureheated up to 230°
  2. temperaturethe reaction mixture was cooled
  3. custompartitioned between methylene chloride and water
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customCrystallization of the residue from ether
  8. customyielded the end product which
  9. customwas recrystallized from ethyl acetate/hexane for analysis, mp 213°-215°

Sources & evidence

ORD record
ord-f535f5b5f7bc4c6cbdf73cb19960e611
Source dataset
uspto-grants-1978_09
Patent number
US04111931

Reaction notes

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