Thionyl Chloride → HCID 20545913, compound

HRID 2059313Notes

Reaction equation

HRID 2059313 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH:19][CH:20]=3)[CH:15](O)[C:14]([CH3:30])([CH3:29])[CH2:13]2)=[CH:8][CH:7]=1>C1C=CC=CC=1>[Cl:3][CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH:17]=2)[CH:12]([C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)[CH2:13][C:14]1([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20545923HCID 20545923, compound

Product 1

HCID 20545913HCID 20545913, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (3 ml) was added dropwise to a stirred solution of 4-(4-chlorophenyl)-1-hydroxy-2,2-dimethyl-7-(2-dimethylaminoethoxy)tetralin (2.0 g) in benzene (50 ml), the temperature being maintained at 5°-10°. After being stirred at room temperature for 16 hr., the solution was taken to dryness in vacuo, the residue shaken with ether-sodium carbonate solution and the ether extract dried (MgSO4). Addition of ethereal hydrogen chloride solution precipitated a viscous oil, which was separated by decantation and redissolved in ethanol. Addition of ether and cooling gave 1-chloro-4-(4-chlorophenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)tetralin as the hydrochloride salt, m.p. 185°-210° approx. (0.93 g, 41%).

Workup

  1. temperaturethe temperature being maintained at 5°-10°
  2. extractionthe ether extract
  3. dry with materialdried (MgSO4)
  4. additionAddition of ethereal hydrogen chloride solution
  5. customprecipitated a viscous oil, which
  6. customwas separated by decantation
  7. dissolutionredissolved in ethanol
  8. additionAddition of ether
  9. temperaturecooling

Sources & evidence

ORD record
ord-2d50d1cc6c114fcdba271e362768dac5
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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