Chloroform → N-(2-{[(4-Bromo-1,2-thiazol-3-yl)methyl]sulfanyl}ethyl)-N'-methylthiourea
Reaction equation
Br.[Br:2][C:3]1[C:4]([CH2:8][S:9][CH2:10][CH2:11][NH2:12])=[N:5][S:6][CH:7]=1.[Na].C(Cl)(Cl)Cl.[CH3:18][N:19]=[C:20]=[S:21]>C(O)C>[CH3:18][NH:19][C:20]([NH:12][CH2:11][CH2:10][S:9][CH2:8][C:4]1[C:3]([Br:2])=[CH:7][S:6][N:5]=1)=[S:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The reaction of 4-bromo-3-(bromomethyl)isothiazole (8.5 g.) with cysteamine (from cysteamine hydrochloride (3.76 g) was performed under conditions similar to those described in Example 57. From the reaction there was obtained 4-bromo-3-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide, which, following recrystallisation from ethanol-ether and acetonitrile, gave needles (4.05 g.) m.p. 111°-112°. The amine base (2.73 g.) was isolated by basification with sodium bydroxide and extraction with chloroform and then dissolved in ethanol and treated with methyl isothiocyanate (0.78 g.) The solution was heated under reflux for 30 minutes, concentrated and the residue triturated with ether to yield the crystalline thiourea (2.9g.) m.p. 60°-61°. Recrystallisation from isopropyl acetate gave N-methyl-N'-[2-((4-bromo-3-isothiazolyl)methylthio)ethyl]thiourea (2.3 g.) as needles, m.p. 62°-63°.
Workup
- customrecrystallisation from ethanol-ether and acetonitrile
- customgave needles (4.05 g.) m.p. 111°-112°
- temperaturewas heated
- temperatureunder reflux for 30 minutes
- concentrationconcentrated
- customthe residue triturated with ether
Sources & evidence
- ORD record
- ord-4454d2328fba4243b49cd2980dd9d7d5
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04104382
Reaction notes
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