Thionyl Chloride → HCID 20227175, compound

HRID 1731734Notes

Reaction equation

HRID 1731734 reaction equation
O[CH2:2][CH:3]1[CH:8]2[C:9]3[C:14]([CH2:15][CH2:16][N:7]2[CH2:6][O:5][CH2:4]1)=[CH:13][C:12]([O:17][CH2:18][CH3:19])=[C:11]([O:20][CH2:21][CH3:22])[CH:10]=3.S(Cl)([Cl:25])=O>C1C=CC=CC=1>[ClH:25].[Cl:25][CH2:2][CH:3]1[CH:8]2[C:9]3[C:14]([CH2:15][CH2:16][N:7]2[CH2:6][O:5][CH2:4]1)=[CH:13][C:12]([O:17][CH2:18][CH3:19])=[C:11]([O:20][CH2:21][CH3:22])[CH:10]=3

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14595359HCID 14595359, compound

Product 1

HCID 20227175HCID 20227175, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.01 mole (3.08 g) of 1-(hydroxymethyl)-9,10-diethoxy-1,6,7,11b-tetrahydro-2H,4H-[1,3]oxazino[4,3-a]-isoquinoline is dissolved in 50 ml of absolute benzene. To the solution 0.05 mole (6 g) of sulfinyl dichloride is added dropwise, under ice cooling and stirring. Thereafter the reaction mixture is slightly refluxed for 3 hours. The excess of the solvent and sulfinyl dichloride is distilled off in vacuo. The residual brown oil is triturated with a small amount of ether to yield the desired compound in crystalline form in a yield of 37%.

Workup

  1. temperatureThereafter the reaction mixture is slightly refluxed for 3 hours
  2. distillationThe excess of the solvent and sulfinyl dichloride is distilled off in vacuo
  3. customThe residual brown oil is triturated with a small amount of ether

Sources & evidence

ORD record
ord-ffec0254cea645158730adb10c5ec57c
Source dataset
uspto-grants-1986_11
Patent number
US04623647

Reaction notes

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