Cyanamide → HCID 178453080, compound

HRID 377090Notes

Reaction equation

HRID 377090 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=1.[N:18]#[C:19][NH2:20]>CCOCC>[ClH:1].[NH:2]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[CH:5][CH:4]=1)[C:19]([NH2:20])=[NH:18]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 70087134tert-Butyl [(4-aminophenyl)methyl]carbamate--hydrogen chloride (1/1)

Product 1

HCID 178453080HCID 178453080, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Amino-N-tert-butoxycarbonylbenzylamine hydrochloride (25.77 g, 99.6 mmol.) and cyanamide (55 g, 1.3 mol.) were heated neat at 65° C. over 1.5 hours. The mixture was then cooled to room temperature and ether (250 mL) was added. The insoluble yellow oil was repeatedly washed with additional ethyl ether to remove traces of cyanamide and dried in vacuo to give 4-guanidino-N-tert-butoxycarbonylbenzylamine hydrochloride as an amorphous yellow material which was carried on without further purification.

Workup

  1. washThe insoluble yellow oil was repeatedly washed with additional ethyl ether
  2. customto remove traces of cyanamide
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b180bc11598e4668884d6408caf1c189
Source dataset
uspto-grants-2000_02
Patent number
US06022969

Reaction notes

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