Isopropanol → N-methyl-S-methyl-N'-[2-(2-dimethylaminomethylthiazol-4-ylmethylthio)ethyl]isothiourea

HRID 279943

반응식

HRID 279943 반응식
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[CH3:3].C(O)(C)C.CS(O)(=O)=O.[CH3:24][N:25]=[C:26](SC)[S:27][CH3:28]>O>[CH3:24][NH:25][C:26](=[N:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[N:9]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[S:6][CH:7]=1)[S:27][CH3:28]

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 6395Methanesulfonic AcidHCID 140427N-Methyl-dithiocarbonimidic acid dimethyl esterHCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

생성물 1

HCID 178484985N-methyl-S-methyl-N'-[2-(2-dimethylaminomethylthiazol-4-ylmethylthio)ethyl]isothiourea

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Ten g. of 2-dimethylaminomethyl-4-(2-aminoethyl)thiomethylthiazole was dissolved in 100 ml. of isopropanol, and 2.8 ml. of methanesulfonic acid was added, followed by 6.5 g. of methylcarbonimidodithioic acid, dimethyl ester. The mixture was stirred under reflux for 16 hours, and was evaporated under vacuum to obtain a residue, which was taken up in 100 ml. of water. The solution was extracted with two 25 ml. portions of dichloromethane, and the aqueous layer was cooled. Fifty ml. of dichloromethane and 15 ml. of 50% aqueous sodium hydroxide were added. The layers were separated, and the solution was extracted again with 50 ml. of dichloromethane. The organic layers were combined, dried over potassium carbonate and evaporated under vacuum to obtain 10.3 g. of product, substantially identical to that of Example 1, which was 96.7% pure by HPLC analysis.

후처리

  1. temperatureunder reflux for 16 hours
  2. customwas evaporated under vacuum
  3. customto obtain a residue, which
  4. extractionThe solution was extracted with two 25 ml
  5. temperatureportions of dichloromethane, and the aqueous layer was cooled
  6. additionof 50% aqueous sodium hydroxide were added
  7. customThe layers were separated
  8. extractionthe solution was extracted again with 50 ml
  9. dry with materialdried over potassium carbonate
  10. customevaporated under vacuum
  11. customto obtain 10.3 g

출처 및 근거

ORD 기록
ord-9f074c3ff4f94a24bfc6dcc9f5024de8
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04587344

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