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

HRID 276291

반응식

HRID 276291 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[S:16][CH2:15][C:14]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[NH:13]1.[OH-].[Na+].[CH:23]1(Br)[CH2:27][CH2:26][CH2:25][CH2:24]1.Cl>CN(C=O)C.O>[CH:23]1([N:13]2[C:14]3([CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:15][S:16][C:12]2=[N:11][C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[CH3:1])[CH2:27][CH2:26][CH2:25][CH2:24]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8728BromocyclopentaneHCID 14798Sodium HydroxideHCID 1784287362-(2-Methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

생성물 1

HCID 99507321-Cyclopentyl-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane수율 26.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
30 °C

실험 절차

A solution of 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane (Method C2a; 33.2 g, 114 mmol) in DMF (1 L) was treated with NaOH (690 g, 17.3 mol) and cyclopentyl bromide (865 mL, 6.3 mol) and the resulting mixture was stirred at 20-40° C. for 18 h, then cooled to 4° C., and treated with water (1.5 L). A conc. HCl solution was added to adjust the pH to 0, and the mixture was extracted with EtOAc (80 mL). The organic phase was washed with a 1N HCl solution (1 L), dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (500 mL) and filtered through a pad of silica gel (9×4 cm). Hexane was added to the resulting solution and volatiles were slowly removed by partial vacuum until crystals formed. The solids were collected to yield 1-cyclopentyl-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane as yellow crystals (10.9 g, 26%): mp 118-9° C.; TLC (5% EtOAc/hex) Rf0.34.

후처리

  1. temperaturecooled to 4° C.
  2. extractionthe mixture was extracted with EtOAc (80 mL)
  3. washThe organic phase was washed with a 1N HCl solution (1 L)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in CH2Cl2 (500 mL)
  7. filtrationfiltered through a pad of silica gel (9×4 cm)
  8. additionHexane was added to the resulting solution and volatiles
  9. customwere slowly removed by partial vacuum until crystals
  10. customformed
  11. customThe solids were collected

출처 및 근거

ORD 기록
ord-2e38565210ba43869010e573a153743f
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

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