Hydrochloric Acid → N,N'-Bis[4-(chloromethyl)phenyl]-N,N'-dimethylurea

HRID 570028Notes

Reaction equation

HRID 570028 reaction equation
[CH3:1][N:2]([C:15]1[CH:20]=[CH:19][C:18](CO)=[CH:17][CH:16]=1)[C:3]([N:5]([CH3:14])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=1)=[O:4].[ClH:23].CCCCCC.[CH:30]([Cl:33])(Cl)Cl>>[CH3:1][N:2]([C:15]1[CH:20]=[CH:19][C:18]([CH2:30][Cl:33])=[CH:17][CH:16]=1)[C:3]([N:5]([CH3:14])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Cl:23])=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 8058HexaneHCID 54431102HCID 54431102, compound

Product 1

HCID 20064895N,N'-Bis[4-(chloromethyl)phenyl]-N,N'-dimethylurea

Procedure

A solution of 10 g N,N'-dimethyl-N,N'-bis(p-hydroxymethylphenyl) urea in 250 ml CHCl3 was stirred vigorously for two hours with 250 ml conc. HCl. The layers were separated, and the organic phase was washed with dilute HCl, dried, and stripped to give a yellow oil. Trituration with hexane caused the product to crystallize. Filtration, washing with hexane, and air drying gave 3.5 g of a fluffy-white crystalline solid which was pure by TLC, m.p. 72°-73° C.

Workup

  1. customThe layers were separated
  2. washthe organic phase was washed with dilute HCl
  3. customdried
  4. customto give a yellow oil
  5. customto crystallize
  6. filtrationFiltration
  7. washwashing with hexane, and air
  8. customdrying

Sources & evidence

ORD record
ord-30702cb4383c4c449f2d0143ecfd9834
Source dataset
uspto-grants-1988_03
Patent number
US04734458

Reaction notes

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