Phosphorus oxychloride → HCID 14986948, compound

HRID 1651537Notes

Reaction equation

HRID 1651537 reaction equation
[C:1]([O:4][CH2:5][CH:6]([N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N+:13]([O-])=[CH:12][C:11]=2[N:10]=[CH:9]1)[CH3:7])(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:24])=O>ClCCl>[C:1]([O:4][CH2:5][CH:6]([N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([Cl:24])[C:11]=2[N:10]=[CH:9]1)[CH3:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14986946HCID 14986946, compound

Product 1

HCID 14986948HCID 14986948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 10.2 g (0.036 mole) of 1-(2-acetoxy-1-methylethyl)-1H-imidazo[4,5-c]quinolin-5-oxide (prepared according to the method of Example 8) in 100 ml of dichloromethane was added in portions, 4.2 ml, 6.9 g (0.45 mole) of phosphorus oxychloride. After 4 hours the mixture was evaporated in vacuo. The residue was added to a saturated sodium bicarbonate solution, and that solution was extracted with chloroform. The chloroform layer was washed with both saturated sodium bicarbonate solution and water, dried over magnesium sulfate and evaporated in vacuo to yield light brown solid 1-(2-acetoxy-1-methylethyl)-4-chloro-1H-imidazo[4,5-c]quinoline.

Workup

  1. customprepared
  2. customAfter 4 hours the mixture was evaporated in vacuo
  3. additionThe residue was added to a saturated sodium bicarbonate solution
  4. extractionthat solution was extracted with chloroform
  5. washThe chloroform layer was washed with both saturated sodium bicarbonate solution and water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-841659d8aba946a7932315a958c22e2b
Source dataset
uspto-grants-1990_05
Patent number
US04929624

Reaction notes

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