Hydrogen Sulfide → 2-Imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine

HRID 5320

반응식

HRID 5320 반응식
[C:1]([N:3]([CH2:14][C:15]#[CH:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)#[N:2].C(N(CC)CC)C.[SH2:24]>CO>[NH:2]=[C:1]1[N:3]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=2)[CH2:14][C:15](=[CH2:16])[S:24]1

참가 물질

5

반응물 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 22416968N-cyano-N-propargyl-3-trifluoromethylaniline

생성물 1

HCID 152396762-Imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of N-cyano-3-trifluoromethylaniline (5.0 g) in acetone (100 ml), potassium carbonate (7.4 g) and propargyl bromide (3.5 g) were added, and the resultant mixture was stirred at room temperature for 10 hours, followed by filtration of the reaction mixture. The solvent was removed from the filtrate by distillation under reduced pressure, and the residue was subjected to column chromatography to give N-cyano-N-propargyl-3-trifluoromethylaniline (3.8 g). The thus obtained N-cyano-N-propargyl-3-trifluoromethylaniline (1 g) and a catalytic amount of triethylamine were dissolved in methanol (30 ml), and the resultant mixture was cooled to 0° C. Hydrogen sulfide was gradually introduced into the mixture for 20 minutes while keeping the temperature at 0° C., followed by introduction of nitrogen gas to remove hydrogen sulfide. The solvent was removed by distillation, and the residue was subjected to column chromatography to give 0.2 g of 2-imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine (Compound (ix)).

후처리

  1. customat 0° C.
  2. customto remove hydrogen sulfide
  3. customThe solvent was removed by distillation

출처 및 근거

ORD 기록
ord-270b39e5107f474fb7cc4aaffd104d14
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244863

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