Acetic Acid → 2-Nitro-1-phenylethyl pyrrolidine-1-carbodithioate

HRID 259452

반응식

HRID 259452 반응식
[N+:1]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].[N:12]1([C:17]([S-:19])=[S:18])[CH2:16][CH2:15][CH2:14][CH2:13]1.[NH4+].C(O)(=O)C>CO>[N:12]1([C:17]([S:19][CH:5]([CH2:4][N+:1]([O-:3])=[O:2])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[S:18])[CH2:16][CH2:15][CH2:14][CH2:13]1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 7626Beta-NitrostyreneHCID 517348Ammonium pyrrolidinedithiocarbamate

생성물 1

HCID 536379742-Nitro-1-phenylethyl pyrrolidine-1-carbodithioate수율 77%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
10 °C

실험 절차

β-Nitrostyrene (7.5 grams, 0.050 mole) was added to a cooled (10° C.) stirred slurry of ammonium 1-pyrrolidinecarbodithioate (8.2 grams, 0.050 mole) in methanol (50 ml.). The temperature of the mixture fell to 5° C., then rapidly climbed to 10° C. The cooling bath was removed and the reaction temperature rose slowly to 22° C. Acetic acid (3.0 grams, 0.05 mole) was added, the slurry was cooled to 10° C. and the solid was filtered off, washed with water, and dried in air. The crude product melted at 108° - 116° C. and weighed 11.4 grams (77% yield). Repeated recrystallizations from cool acetone-methanol, hot acetone-2-propanol, and cool methylene chloride-toluene-hexane solutions gave pure α-(nitromethyl)benzyl 1-pyrrolidinecarbodithioate melting at 116° - 120° C. (sintering at 113° C.).

후처리

  1. customfell to 5° C.
  2. customrapidly climbed to 10° C
  3. customThe cooling bath was removed
  4. customrose slowly to 22° C
  5. temperaturethe slurry was cooled to 10° C.
  6. filtrationthe solid was filtered off
  7. washwashed with water
  8. customdried in air
  9. customrecrystallizations
  10. temperaturefrom cool acetone-methanol, hot acetone-2-propanol
  11. temperaturecool methylene chloride-toluene-hexane solutions

출처 및 근거

ORD 기록
ord-7efb0e60deca4a4081e2eea946282b06
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04038288

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