Ethylenediamine → N-methyl-N'-[2-((5-benzyl-4-oxazolyl)methylamino)ethyl]thiourea

HRID 27561Notes

Reaction equation

[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH2:5]([C:12]1[O:16][CH:15]=[N:14][C:13]=1[CH2:17]Cl)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:19][N:20]=[C:21]=[S:22]>>[CH3:19][NH:20][C:21]([NH:3][CH2:2][CH2:1][NH:4][CH2:17][C:13]1[N:14]=[CH:15][O:16][C:12]=1[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[S:22]

Participants

Reactant 3

HCID 3301Ethylenediamine

HCID 11167Methyl isothiocyanate

HCID 205578365-Benzyl-4-chloromethyloxazole

Product 1

HCID 20557842N-methyl-N'-[2-((5-benzyl-4-oxazolyl)methylamino)ethyl]thiourea

Procedure

Reacting ethylenediamine with 5-benzyl-4-chloromethyloxazole by the procedure of Example 34, then reacting the resulting N-(5-benzyl-4-oxazolymethyl)-ethylenediamine with methyl isothiocyanate by the procedure of Example 3(b) and chromatographing gives N-methyl-N'-[2-((5-benzyl-4-oxazolyl)methylamino)ethyl]-thiourea. Reacting this thiourea with lead cyanamide by the procedure of Example 3(b) gives N-[2-((5-benzyl-4-oxaxzolyl)methylamino)ethyl]-N'-cyano-N"-methylguanidine

Sources & evidence

ORD record: ord-d4d9dab81cf84ccea407e430e8a429ab
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04221802

Reaction notes

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