Methyl isothiocyanate → N-Methyl-N'-(2-{[(1,2-thiazol-3-yl)methyl]sulfanyl}ethyl)thiourea

HRID 329097ノート

反応式

HRID 329097 の反応式
Cl.[NH2:2][CH2:3][CH2:4][S:5][CH2:6][C:7]1[CH:11]=[CH:10][S:9][N:8]=1.[CH3:12][N:13]=[C:14]=[S:15]>C(O)C>[CH3:12][NH:13][C:14]([NH:2][CH2:3][CH2:4][S:5][CH2:6][C:7]1[CH:11]=[CH:10][S:9][N:8]=1)=[S:15]

参加物

4

反応物 2

HCID 11167Methyl isothiocyanateHCID 205502093-[(2-Aminoethyl)thiomethyl]isothiazole hydrochloride

生成物 1

HCID 20466672N-Methyl-N'-(2-{[(1,2-thiazol-3-yl)methyl]sulfanyl}ethyl)thiourea

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution was prepared by the gradual addition of cysteamine hydrochloride (2.03 g.) to sodium (0.83 g.) dissolved in ethanol (50 ml.) with stirring at 0° under a nitrogen atmosphere. After stirring for 2 hours at 0°, 3-bromomethylisothiazole (3.2 g.) was added dropwise over 15 minutes at 0°, the reaction mixture subsequently being set aside overnight at room temperature. Following acidification to pH 3.5 with hydrochloric acid, concentration and re-evaporation with ethanol, the residue was dissolved in ethanol, filtered and concentrated to yield 3-[(2-aminoethyl)thiomethyl]isothiazole hydrochloride (3.5 g.). This was converted directly to the free base by treatment with aqueous potassium carbonate and extraction with ether. The extracts were dried over magnesium sulphate, filtered and concentrated to yield the amine base as an oil (1.56 g.). The amine was dissolved in ethanol (10 ml.), methyl isothiocyanate (0.66 g.) added, and the solution heated under reflux for 30 minutes. Concentration, followed by purification of the crude product by chromatography on a column of silica gel with ethyl acetate as eluant followed by chromatography on a column of alumina with benzene/ethyl acetate as eluant gave N-methyl-N'-[2-(3-isothiazolylmethylthio)ethyl]thiourea. (Found: C, 38.9; H, 5.4 N, 16.5; S, 38.3. C8H13N3S3 requires: C, 38.8; H, 5.3; N, 17.0; S, 38.9).

後処理

  1. extractionThis was converted directly to the free base by treatment with aqueous potassium carbonate and extraction with ether
  2. dry with materialThe extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield the amine base as an oil (1.56 g.)
  6. temperaturethe solution heated
  7. temperatureunder reflux for 30 minutes
  8. concentrationConcentration
  9. customfollowed by purification of the crude product by chromatography on a column of silica gel with ethyl acetate as eluant

出典と根拠

ORDレコード
ord-1527f244695c453c843e5b70a53e63ca
出典データセット
uspto-grants-1977_04
特許番号
US04018931

反応ノート

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