Hydrochloric Acid → HCID 53954328, compound

HRID 839524Notes

Reaction equation

HRID 839524 reaction equation
C(N[S:4](=[O:7])(=O)[OH:5])C.C=O.[ClH:10].S(Cl)([Cl:13])=O.P(Cl)(Cl)(Cl)(Cl)Cl.[N:21]1[CH:26]=CC=[CH:23][CH:22]=1>ClCCCl>[CH2:22]([N:21]([CH2:26][Cl:13])[S:4]([Cl:10])(=[O:7])=[O:5])[CH3:23]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 24819Phosphorus pentachlorideHCID 244259Ethylsulfamic acid

Product 1

HCID 53954328HCID 53954328, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
83 °C

Procedure

A suspension of 93.8 parts of ethylsulfamic acid and 27 parts of paraformaldehyde in 650 parts of 1,2-dichloroethane is saturated with hydrogen chloride (72 parts) at from 10° to 15° C, whilst stirring. 0.2 part of pyridine and 142.8 parts of thionyl chloride are then added in the course of 15 minutes at 15° C. The reaction mixture is stirred for 1/2 hour at 25° C and 11/2 hour under reflux. 83.5 parts of phosphorus pentachloride are then added and the mixture is stirred for 4 hours under reflux (83° C) until the evolution of gas has ceased. On concentrating under reduced pressure, and distilling, 84 parts (58% of theory) of N-ethyl-N-chloromethylsulfamic acid chloride of boiling point 70°-75° C/0.1 mbar and nD25 = 1.4800 are obtained.

Workup

  1. stirringThe reaction mixture is stirred for 1/2 hour at 25° C
  2. temperature11/2 hour under reflux
  3. stirringthe mixture is stirred for 4 hours
  4. concentrationOn concentrating under reduced pressure
  5. distillationdistilling

Sources & evidence

ORD record
ord-e5e39f49da1742e0ba950e242af8ea7a
Source dataset
uspto-grants-1978_06
Patent number
US04096181

Reaction notes

Loading…