Methyl isothiocyanate → HCID 20466711, compound

HRID 1974386Notes

Reaction equation

HRID 1974386 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1.[CH3:11][N:12]=[C:13]=[S:14]>C(O)C.C(OCC)(=O)C>[CH3:11][NH:12][C:13]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1)=[S:14]

Participants

5

Reactant 2

HCID 11167Methyl isothiocyanateHCID 179312574-(1,3-Thiazol-2-yl)butan-1-amine

Product 1

HCID 20466711HCID 20466711, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Phthalimidobutyl)thiazole (5.0 g) is hydrolysed with hydrochloric acid in the usual way. The amine hydrochloride obtained is basified with potassium carbonate and extracted with ether-ethanol (3:1) to give 2-(4-amino-butyl)thiazole as a colourless oil. The reaction of the amine (2.0 g) and methyl isothiocyanate (0.98 g) in ethanol (10 ml) for 1 hour, followed by chromatography of the product on silica gel with ethyl acetate as eluent gives N-methyl-N'-(4-(2-thiazolyl)butyl) thiourea (2.5 g) as a colourless oil. Formation of the hydrobromide salt yields a crystalline solid, m.p. 130°-132° C.

Sources & evidence

ORD record
ord-f9c66bd070f74334b08a2dea3fd5abe1
Source dataset
uspto-grants-1976_12
Patent number
US04000302

Reaction notes

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