Sodium Cyanate → N-[5-(2-aminoethyl)-2-benzyloxyphenyl]urea

HRID 1032538Notes

Reaction equation

HRID 1032538 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([CH:11]=1)[NH2:10].[O-:20][C:21]#[N:22].[Na+]>C(O)(=O)C.O.Cl>[NH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([NH:10][C:21]([NH2:22])=[O:20])[CH:11]=1

Participants

6

Reactant 2

HCID 517096Sodium CyanateHCID 1317165715-(2-Aminoethyl)-2-benzyloxyaniline, hydrochloride

Product 1

HCID 13629323N-[5-(2-aminoethyl)-2-benzyloxyphenyl]ureaYield 22.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

2.4 g of 5-(2-aminoethyl)-2-benzyloxyaniline, hydrochloride, is dissolved in a mixture of 20 ml of acetic acid, 5 ml of water and 0.5 ml of 2N hydrochloric acid. A solution of 0.72 g of sodium cyanate in 5 ml of water is added and the mixture is stirred for one hour at room temperature. Thereafter, the mixture is diluted with 100 ml of water, the product is extracted by shaking with methylene chloride and recrystallized from isopropanol, thus obtaining 0.56 g of N-[5-(2-aminoethyl)-2-benzyloxyphenyl]urea, mp 176°-180° C.

Workup

  1. extractionthe product is extracted
  2. stirringby shaking with methylene chloride
  3. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-38829b00fdbf4091a1a9116d05e6e71b
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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