Ethylenediamine → N-cyano-N'-ethyl-N"-[2-((4-methyl-5-oxazolyl)methylamino)ethyl]guanidine

HRID 1605369Notes

Reaction equation

HRID 1605369 reaction equation
ClC[C:3]1O[CH:6]=[N:5][C:4]=1C.[CH2:9]([NH2:12])CN.[CH3:13][C:14]1[N:15]=[CH:16][O:17][C:18]=1[CH2:19][NH:20][CH2:21][CH2:22][NH2:23].C([N:26]=C=S)C>>[C:9]([NH:12][C:6]([NH:5][CH2:4][CH3:3])=[N:23][CH2:22][CH2:21][NH:20][CH2:19][C:18]1[O:17][CH:16]=[N:15][C:14]=1[CH3:13])#[N:26]

Participants

5

Reactant 4

HCID 3301EthylenediamineHCID 10966Ethyl isothiocyanateHCID 2054855-(Chloromethyl)-4-methyl-1,3-oxazoleHCID 14009880N-(4-methyl-5-oxazolylmethyl)ethylenediamine

Product 1

HCID 57257796N-cyano-N'-ethyl-N"-[2-((4-methyl-5-oxazolyl)methylamino)ethyl]guanidine

Procedure

Reacting of 5-chloromethyl-4-methyloxazole with ethylenediamine by the procedure of Example 34 and reaction of the resulting N-(4-methyl-5-oxazolylmethyl)ethylenediamine with ethyl isothiocyanate by the procedure of Example 3(b) gives, after purifying by column chromatography, N-ethyl-N'-[2-(4-methyl-5-oxazolylmethylamino)ethyl]thiourea. This thiourea is reacted with lead cyanamide by the procedure of Example 3(b) to give N-cyano-N'-ethyl-N"-[2-((4-methyl-5-oxazolyl)methylamino)ethyl]guanidine.

Workup

  1. customgives
  2. customafter purifying by column chromatography, N-ethyl-N'-[2-(4-methyl-5-oxazolylmethylamino)ethyl]thiourea
  3. customThis thiourea is reacted with lead cyanamide by the procedure of Example 3(b)

Sources & evidence

ORD record
ord-0a75d4bdcd33493686bd7d643ccb9872
Source dataset
uspto-grants-1976_04
Patent number
US03950333

Reaction notes

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