Chloroform → N-(2-{[(4-Bromo-1,2-thiazol-3-yl)methyl]sulfanyl}ethyl)-N'-methylthiourea

HRID 329099

Reaction equation

HRID 329099 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.[OH-].[Na+].C(Cl)(Cl)Cl.[CH3:19][N:20]=[C:21]=[S:22]>C(O)C>[CH3:19][NH:20][C:21]([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:22]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11167Methyl isothiocyanateHCID 14798Sodium HydroxideHCID 205500984-Bromo-3-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide

Product 1

HCID 12923381N-(2-{[(4-Bromo-1,2-thiazol-3-yl)methyl]sulfanyl}ethyl)-N'-methylthioureaYield 108.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 122. 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 hydroxide 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 (2.9 g.) 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°. (Found: C, 29.5; H, 3.8; N, 12.9; Br, 24.6; S, 29.3. C8H12BrN3S3 requires: C, 29.5; H, 3.7; N, 12.9; Br, 24.5; S, 29.5).

Workup

  1. customrecrystallisation from ethanol-ether and acetonitrile
  2. customgave needles (4.05 g.), m.p. 111°-112°
  3. temperatureThe solution was heated
  4. temperatureunder reflux for 30 minutes
  5. concentrationconcentrated
  6. customthe residue triturated with ether

Sources & evidence

ORD record
ord-ede7199084b34cb698e515f7cac7a3b1
Source dataset
uspto-grants-1977_04
Patent number
US04018931

Linked notes

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