Hydrochloric Acid → HCID 69508588, compound

HRID 1354344Notes

Reaction equation

HRID 1354344 reaction equation
Cl.[Cl:2][CH2:3][CH2:4]N.[N:6]1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.Cl>ClCCl.O>[Cl:2][CH2:3][CH2:4][C:16]1([S:19]([NH2:6])(=[O:21])=[O:20])[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH2:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 69508588HCID 69508588, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

11.6 g (100 mmol) of 2-chloroethylamine HCl were suspended in dichloromethane. 13.8 g (175 mmol) of pyridine were added, the mixture was stirred for 10 minutes and then 15.8 g (75 mmol) of 4-chlorobenzenesulfonyl chloride, dissolved in dichloro-methane, were added dropwise. The reaction mixture was heated under reflux for 8-10 hours, then treated with water and adjusted to a pH of 1-2 using HCl. The organic phase was washed three times with 3% strength HCl and the aqueous phase was extracted by shaking 3-4 times with dichloromethane. The combined organic phases were dried using Na2SO4, evaporated in the and recrystallized from ethanol. The yield was 11 g.

Workup

  1. additionwere added dropwise
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 8-10 hours
  4. washThe organic phase was washed three times with 3% strength HCl
  5. extractionthe aqueous phase was extracted
  6. stirringby shaking 3-4 times with dichloromethane
  7. customThe combined organic phases were dried
  8. customevaporated in the and
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ba29ff54c97341c2873044f9b0678639
Source dataset
uspto-grants-2007_05
Patent number
US07223781B2

Reaction notes

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