Methyl isothiocyanate → N-(2-dimethylaminoethyl)-N'-[2-(3-isothiazolylmethylamino)ethyl]thiourea

HRID 1834296Notes

Reaction equation

CN=C=S.[S:5]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH2:12][CH2:13][NH2:14])=[N:6]1.[CH3:15][N:16]([CH3:22])[CH2:17][CH2:18][N:19]=[C:20]=[S:21]>>[CH3:15][N:16]([CH3:22])[CH2:17][CH2:18][NH:19][C:20]([NH:14][CH2:13][CH2:12][NH:11][CH2:10][C:7]1[CH:8]=[CH:9][S:5][N:6]=1)=[S:21]

Participants

Reactant 3

HCID 11167Methyl isothiocyanate

HCID 3853726(2-Isothiocyanatoethyl)dimethylamine

HCID 20557777N-(3-isothiazolylmethyl)ethylenediamine

Product 1

HCID 20557944N-(2-dimethylaminoethyl)-N'-[2-(3-isothiazolylmethylamino)ethyl]thiourea

Procedure

By the procedure of Example 40(a) (ii), N-(3-isothiazolylmethyl)ethylenediamine is reacted with 2-dimethylaminoethyl isothiocyanate to give N-(2-dimethylaminoethyl)-N'-[2-(3-isothiazolylmethylamino)ethyl]thiourea. Reacting with hydrobromic acid gives the hydrobromide salt.

Sources & evidence

ORD record: ord-9f2f8888e2e345c2aedfb2dab568e94e
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04069327

Reaction notes

Loading…