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

HRID 326787

反応式

HRID 326787 の反応式
[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]

参加物

8

反応物 4

HCID 280Carbon DioxideHCID 7679Phenylacetyl chloride2 回HCID 10112Calcium CarbonateHCID 195716Ici 222155

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-da9f480164f94d9599cd4275cfc57a51
出典データセット
uspto-grants-1993_12
特許番号
US05270342

関連ノート

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