Phosphorus oxychloride → 4-Chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-difluoromethoxy-phthalazine

HRID 2268900Notes

Reaction equation

HRID 2268900 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:24])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH:20]([F:22])[F:21])=[CH:16][CH:17]=2)[C:12](=O)[NH:11][N:10]=1.O=P(Cl)(Cl)[Cl:27]>C(#N)C>[Cl:27][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:19][CH:20]([F:22])[F:21])[CH:14]=2)[C:9]([CH2:8][C:7]2[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=2[Cl:24])=[N:10][N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 183816054-(3,5-Dichloro-pyridin-4-ylmethyl)-7-difluoromethoxy-2H-phthalazin-1-one

Product 1

HCID 183816244-Chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-difluoromethoxy-phthalazineYield 97.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-difluoromethoxy-2H-phthalazin-1-one (6.64 g, 17.8 mmoles), prepared as described in example 98, in acetonitrile (70 ml), under N2, was added with POCl3 (8.3 ml, 89 mmoles). After 4.5 hours under reflux and 1 night to stand, the mixture was dried under vacuum, taken up in CH2Cl2 and washed with an aqueous Na2CO3 solution, then discoloured with charcoal, filtered over celite and dried again to give 6.8 g of the title compound (yield: 97%).

Workup

  1. customprepared
  2. temperatureAfter 4.5 hours under reflux and 1 night
  3. customthe mixture was dried under vacuum
  4. washwashed with an aqueous Na2CO3 solution
  5. filtrationfiltered over celite
  6. customdried again

Sources & evidence

ORD record
ord-9973f25711a04d17a2c40f7f25da24c2
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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