Potassium Hydroxide → 4-Benzyloxyphenylcyanamide

HRID 1464062Notes

Reaction equation

HRID 1464062 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH2:20])=S)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.O.O.C([O-])(=O)C.[Pb+2].C([O-])(=O)C>O>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]#[N:20])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 22456Lead diacetate trihydrateHCID 2060579(4-(Benzyloxy)phenyl)thiourea

Product 1

HCID 190892954-Benzyloxyphenylcyanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A hot solution of potassium hydroxide (25.2 g) in water (70 ml) was added to N-(4-benzyloxyphenyl)thiourea (11.34 g) suspended in boiling water (80 ml). A hot solution of lead acetate trihydrate (71.5 g) in water (80 ml) was added and the mixture heated under reflux for an hour and filtered whilst hot. The filtrate was cooled, acidified to pH 7 with acetic acid and extracted with dichloromethane to give 4-benzyloxyphenylcyanamide as a white solid which was purified by flash chromatography (as described by Still et al in J Org Chem, 1978, 43, 2923-2925) over silica using hexane and chloroform as eluant to give 4-benzyloxyphenylcyanamide (m.p. 105° C.).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for an hour
  3. filtrationfiltered whilst hot
  4. temperatureThe filtrate was cooled
  5. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-f1cc0ab2960948768da935fd94b29023
Source dataset
uspto-grants-1994_04
Patent number
US05302720

Reaction notes

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