Phosphorus oxychloride → HCID 22627980, compound

HRID 278625Notes

Reaction equation

HRID 278625 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([S:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([C:23]4[S:27][C:26]([C:28]5[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=5)=[N:25][C:24]=4[CH3:34])=[O:22])[CH2:17][CH2:16]3)(=[O:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:38])=O>>[Cl:38][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][C:7]=1[S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[S:27][C:26]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[N:25][C:24]=2[CH3:34])=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178432592HCID 178432592, compound

Product 1

HCID 22627980HCID 22627980, compound

Procedure

A suspension of 1-(7-chloro-4-hydroxyquinoline-3-sulfonyl)-4-[4-methyl-2-(4-pyridyl)-5-thiazolecarbonyl]-piperazine (200 mg) in phosphoryl chloride (6 ml) was refluxed for 2 hours. The reaction mixture was concentrated, and ice water was added to the residue. To the mixture was added an aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with dichloromethane. The extract was dried and concentrated to give brown crystals of the title compound (223 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionice water was added to the residue
  4. additionTo the mixture was added an aqueous solution of sodium hydrogen carbonate
  5. extractionthe mixture was extracted with dichloromethane
  6. customThe extract was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-38f9ae34527e485c8ea991fba25063d8
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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