Hydrochloric Acid → HCID 21416964, compound

HRID 442257Notes

Reaction equation

HRID 442257 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4].C(Cl)(Cl)[Cl:19].C1N2CN3CN(C2)C[N:23]1C3.Cl>C(O)C>[ClH:19].[CH3:16][N:15]([CH3:17])[S:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][NH2:23])=[CH:6][CH:7]=1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 6212ChloroformHCID 21416941HCID 21416941, compound

Product 1

HCID 21416964HCID 21416964, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-[4-(Bromoacetyl)phenyl]-N', N'-dimethylsulfamide (32 g., 0.10 mole) is added dropwise to a chloroform solution of hexamethylenetetramine (21.0 g., 0.15 mole) and the mixture is stirred overnight to give 42.6 g. of the complex. This is hydrolyzed by heating 0.5 hr. with 40 ml. conc. HCl and 500 ml. abs. ethanol. The mixture is cooled and the insoluble ammonium chloride is removed. The solution is concentrated in vacuo and the residue is triturated with isopropanol to give 27.3 g. of intermediate which is washed with water and recrystallized from methanol-isopropyl ether, m.p. 159-159.5° C. (dec.)

Workup

  1. customto give 42.6 g
  2. temperatureThis is hydrolyzed by heating 0.5 hr
  3. temperatureThe mixture is cooled
  4. customthe insoluble ammonium chloride is removed
  5. concentrationThe solution is concentrated in vacuo
  6. customthe residue is triturated with isopropanol
  7. customto give 27.3 g
  8. washof intermediate which is washed with water
  9. customrecrystallized from methanol-isopropyl ether, m.p. 159-159.5° C. (dec.)

Sources & evidence

ORD record
ord-583e22de8a394d4ea03201068cdd4a61
Source dataset
uspto-grants-1977_08
Patent number
US04044151

Reaction notes

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