Hydrochloric Acid → 3-Chlorobenzylurea

HRID 2305384Notes

Reaction equation

HRID 2305384 reaction equation
[O-:1][C:2]#[N:3].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][NH2:10].Cl>O.C1COCC1>[Cl:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][NH:10][C:2]([NH2:3])=[O:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 77802Benzenemethanamine, 3-chloro-HCID 517096Sodium Cyanate

Product 1

HCID 27325773-Chlorobenzylurea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.22 g of sodium cyanate was added to a solution of 5.50 ml of 3-chlorobenzylamine in 40 ml of water and 40 ml of THF followed by dropwise addition of 48.6 ml of 1N HCl. After 3 days, the mixture was evaporated to dryness, the residue extracted with hot THF and the filtrate again evaporated to dryness. The residue was suspended in 180 ml of diethyl ether and the solid collected to give the title compound (7.91 g) as a white solid.

Workup

  1. customthe mixture was evaporated to dryness
  2. extractionthe residue extracted with hot THF
  3. customthe filtrate again evaporated to dryness
  4. customthe solid collected

Sources & evidence

ORD record
ord-15aeb694257b436388383be6f59fc290
Source dataset
uspto-grants-2002_08
Patent number
US06440979B1

Reaction notes

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