Chloroform → HCID 13044649, compound

HRID 1980569Notes

Reaction equation

HRID 1980569 reaction equation
Cl.O=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:13]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH:23]([O:30][CH2:31][CH3:32])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:18][CH2:17]3)(=[O:15])=[O:14])[CH:11]=2)[N:6]=[CH:5][NH:4]1.S(Cl)([Cl:35])=O.CN(C)C=O.C(Cl)(Cl)Cl>O>[Cl:35][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:13]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH:23]([O:30][CH2:31][CH3:32])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:18][CH2:17]3)(=[O:15])=[O:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 135702407HCID 135702407, compound

Product 1

HCID 13044649HCID 13044649, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 9.57 g of 1-(3,4-dihydro-4-oxo-6-quinazolinesulfonyl)-4-(2-ethoxy-2-phenylethyl)piperazine hydrochloride were added 40 ml of thionyl chloride and 4.8 ml of N,N-dimethylformamide, and the mixture was refluxed under heating. To the residue thus obtained were added 60 ml of chloroform and 30 ml of a mixture of ice and water, and the mixture was stirred under cooling with ice. Then the chloroform layer was separated therefrom and the aqueous layer was extracted with chloroform and the chloroform layer obtained was combined with the one previously separated. The chloroform layer was washed with, in order, water, a saturated sodium bicarbonate solution and water, and then dried with Glauber's salt. The chloroform layer thus obtained was condensed under reduced pressure to give 7.33 g of 1-(4-chloro-6-quinazolinesulfonyl)-4-(2-ethoxy-2-phenylethyl)piperazine as an oily substance in a yield of 80%.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating
  3. customTo the residue thus obtained
  4. temperatureunder cooling with ice
  5. customThen the chloroform layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. customthe chloroform layer obtained
  8. custompreviously separated
  9. washThe chloroform layer was washed with, in order, water
  10. dry with materiala saturated sodium bicarbonate solution and water, and then dried with Glauber's salt
  11. customThe chloroform layer thus obtained
  12. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-b9e27c0c862d4d1fb60a4d0603748ad4
Source dataset
uspto-grants-1985_04
Patent number
US04510307

Reaction notes

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