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

HRID 326787Notes

Reaction equation

HRID 326787 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-da9f480164f94d9599cd4275cfc57a51
Source dataset
uspto-grants-1993_12
Patent number
US05270342

Reaction notes

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