Carbon Dioxide → HCID 9951696, compound

HRID 1655411Notes

Reaction equation

HRID 1655411 reaction equation
[O:1]([CH2:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Ca+2].[NH2:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([S:25]([CH2:28][N+:29]([O-:31])=[O:30])(=[O:27])=[O:26])=[C:20]([CH3:32])[CH:19]=1.C(=O)=O.Cl>O1CCCC1.C(OCC)(=O)C.O>[CH3:24][C:22]1[CH:23]=[C:18]([NH:17][C:9](=[O:10])[CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:19]=[C:20]([CH3:32])[C:21]=1[S:25]([CH2:28][N+:29]([O-:31])=[O:30])(=[O:27])=[O:26]

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 10112Calcium CarbonateHCID 69703Phenoxyacetyl chlorideHCID 195716Ici 222155

Product 1

HCID 9951696HCID 9951696, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenoxyacetyl chloride (427 mg, 2.5 mM) was added to a stirred suspension of calcium carbonate (300 mg, 3 mM) and (4-amino-2,6-dimethylphenylsulfonyl)nitromethane (488 mg, 2 mM) in dry tetrahydrofuran (THF; 2.5 mL). The mixture was stirred for 30 minutes during which time carbon dioxide was released. Water (10 mL) and ethyl acetate (30 mL) were then added and the mixture acidified with 2M hydrochloric acid to pH 3. The organic phase was separated and washed with saturated sodium chloride solution (2×10 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-[2-phenoxyacetamido]phenylsulfonyl)nitromethane as white crystals, having m.p. 166°-167° C. and in 67% yield after recrystallisation from ethyl acetate/hexane; microanalysis, found: C, 54.1; H, 5.1; N, 7.3%; C17H18N2O6S requires: C, 54.0: H, 4.8; N, 7.4%.

Workup

  1. customThe organic phase was separated
  2. washwashed with saturated sodium chloride solution (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated
  5. customthe residue recrystallised from ethyl acetate
  6. customThe solid obtained
  7. washwas washed with ether and air
  8. customdried

Sources & evidence

ORD record
ord-a03b2cc75d5346da84be4a30dc26d7ff
Source dataset
uspto-grants-1993_10
Patent number
US05250570

Reaction notes

Loading…