Hydrochloric Acid → 3-Chlorobenzylurea

HRID 1108235Notes

Reaction equation

HRID 1108235 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-d3dd997dda6149dc8969f873e31210c9
Source dataset
uspto-grants-2000_05
Patent number
US06066641

Reaction notes

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