Thionyl Chloride → HCID 13106290, compound

HRID 275108Notes

Reaction equation

HRID 275108 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]1[CH:30]=[CH:29][CH:28]=[CH:27][C:6]=1[O:7][CH2:8][CH2:9][NH:10][CH:11]([CH3:26])[CH:12]([C:14]1[CH:15]=[CH:16][C:17]([O:24][CH3:25])=[C:18]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:19]=1)O)[CH3:3].S(Cl)([Cl:33])=O>C(#N)C>[ClH:33].[Cl:1][CH:12]([C:14]1[CH:15]=[CH:16][C:17]([O:24][CH3:25])=[C:18]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:19]=1)[CH:11]([NH:10][CH2:9][CH2:8][O:7][C:6]1[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=1[O:4][CH2:2][CH3:3])[CH3:26]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13564370HCID 13564370, compound

Product 1

HCID 13106290HCID 13106290, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 1,000 ml of acetonitrile was suspended 17 g of 5-{2-[2-(2-ethoxyphenoxy)ethylamino]-1-hydroxy-2-methylethyl}-2-methoxybenzenesulfonamide hydrochloride and while stirring the suspension, 9 g of thionyl chloride was added dropwise to the suspension at room temperature, whereby the product first dissolved and then began to crystallize gradually. After stirring the mixture for two days, the crystals formed were recovered by filtration, washed with chloroform and dried to provide 15 g of 5-{1-chloro-2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl}-2-methoxybenzenesulfonamide hydrochloride.

Workup

  1. additionwas added dropwise to the suspension at room temperature
  2. dissolutionwhereby the product first dissolved
  3. customto crystallize gradually
  4. customthe crystals formed
  5. filtrationwere recovered by filtration
  6. washwashed with chloroform
  7. customdried

Sources & evidence

ORD record
ord-2eeb919c4cf7456988502e2b0d8d512f
Source dataset
uspto-grants-1995_02
Patent number
US05391825

Reaction notes

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