Carbon Dioxide → (2,6-Dimethyl-4-[phenylacetamido]phenylsulfonyl)nitromethane

HRID 326787

반응식

HRID 326787 반응식
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Ca+2].[NH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([S:24]([CH2:27][N+:28]([O-:30])=[O:29])(=[O:26])=[O:25])=[C:19]([CH3:31])[CH:18]=1.C(=O)=O>O1CCCC1.C(OCC)(=O)C.C(O)C>[CH3:23][C:21]1[CH:22]=[C:17]([NH:16][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:18]=[C:19]([CH3:31])[C:20]=1[S:24]([CH2:27][N+:28]([O-:30])=[O:29])(=[O:26])=[O:25]

참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 7679Phenylacetyl chloride2회HCID 10112Calcium CarbonateHCID 195716Ici 222155

생성물 1

HCID 9928921(2,6-Dimethyl-4-[phenylacetamido]phenylsulfonyl)nitromethane수율 54%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Phenylacetyl chloride (1.16 g, 7.5 mM) was added to a stirred suspension of calcium carbonate (1.0 g, 10.0 mM) and (4-amino-2,6-dimethylphenylsulfonyl)nitromethane (1.22g, 5.0 mM) in dry tetrahydrofuran (THF; 20 mL). The mixture was stirred for 16 hours during which time carbon dioxide was slowly released. Ethanol (1.0 mL) was then added and the mixture stirred for a further hour in order to decompose excess phenylacetyl chloride. Ethyl acetate (100 mL) was then added and the insoluble material removed by filtration. The filtrate was washed first with water (50 mL) containing 2M hydrochloric acid (2.0 mL) and then with saturated sodium chloride solution (2×40 mL) and then dried (MgSO4). The solvent was evaporated and the residue recrystallised from ethyl acetate. The solid obtained was washed with ether and air dried to give (2,6-dimethyl-4-[phenylacetamido]phenylsulfonyl)nitromethane as white crystals, having m.p. 158°-159° C. and in 54 % yield after recrystallisation from ethanol; microanalysis, found: C, 56.7; H, 5.0; N, 8.0%; C17H18N2O5S requires: C, 56.4: H, 5.0; N, 7.7%.

후처리

  1. customthe insoluble material removed by filtration
  2. washThe filtrate was washed first with water (50 mL)
  3. additioncontaining 2M hydrochloric acid (2.0 mL)
  4. dry with materialwith saturated sodium chloride solution (2×40 mL) and then dried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue recrystallised from ethyl acetate
  7. customThe solid obtained
  8. washwas washed with ether and air
  9. customdried

출처 및 근거

ORD 기록
ord-da9f480164f94d9599cd4275cfc57a51
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270342

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