Hydrochloric Acid → 2-(2-Methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

HRID 276276

반응식

HRID 276276 반응식
[NH2:1][C:2]1([CH2:7]O)[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.O=S(Cl)Cl.[CH3:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]=[C:25]=[S:26].CN1CCOCC1>ClCCCl>[CH3:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]=[C:25]1[S:26][CH2:7][C:2]2([CH2:6][CH2:5][CH2:4][CH2:3]2)[NH:1]1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 24386Thionyl ChlorideHCID 663071-AminocyclopentanemethanolHCID 1456212-Methyl-4-nitrophenyl isothiocyanate

생성물 1

HCID 1784287362-(2-Methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane수율 81.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
100 °C

실험 절차

To a solution of 1-amino-1-(hydroxymethyl)cyclopentane (Method B1c; 20.7 g, 180 mmol) and HCl (4M in p-dioxane, 400 mL) was added SOCl2 (15.7 mL, 216 mmol) and the resulting solution was heated at 100° C. for 18 h. The reaction mixture was concentrated under reduced pressure, then treated with 2-methyl4-nitrophenyl isothiocyanate (31.4 g, 162 mmol) and 1,2-dichloroethane (400 ml), followed by N-methylmorpholine (49 mL, 449 mmol). The resulting mixture was heated at 70° C. for 18 h, cooled to room temp. and concentrated under reduced pressure. The residue was treated with hot EtOAc, filtered and concentrated under reduced pressure. The residue was recrystallized (MeOH) to yield 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane (38.3 g, 81%): TLC (25% EtOAc/hex) Rf0.27.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. temperatureThe resulting mixture was heated at 70° C. for 18 h
  3. temperaturecooled to room temp.
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was treated with hot EtOAc
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized (MeOH)

출처 및 근거

ORD 기록
ord-1efd6c0cc5dd43dd9c312244b3ed4f4b
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

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