4-Nitrophenyl chloroformate → HCID 22890091, compound

HRID 966465Notes

Reaction equation

HRID 966465 reaction equation
[S:1]([CH2:7][CH2:8][OH:9])([CH2:4][CH2:5][OH:6])(=[O:3])=[O:2].Cl[C:11]([O:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:12]>N1C=CC=CC=1>[OH:6][CH2:5][CH2:4][S:1]([CH2:7][CH2:8][O:9][C:11]([O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1)=[O:12])(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 929332,2'-Sulfonyl bisethanol

Product 1

HCID 22890091HCID 22890091, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2,2′-sulfonyldiethanol (4.85 g, 39.75 mmol) and p-nitrophenyl chloroformate (2.0 g, 9.92 mmol), in 20 ml of dry pyridine, was stirred for 2 h at room temperature and then evaporated to dryness. The residue was dissolved in 350 ml of ethyl acetate and washed with water (4×100 ml). The organic solution was dried over sodium sulfate, filtered and evaporated. The crude product was purified by silica gel chromatography, eluting with ethyl acetate. The pure product fractions were pooled and evaporated affording an oil: 0.68 g (22%) yield.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in 350 ml of ethyl acetate
  3. washwashed with water (4×100 ml)
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with ethyl acetate
  9. customevaporated
  10. customaffording an oil
  11. custom0.68 g (22%) yield

Sources & evidence

ORD record
ord-8a46816c05854fa0a825778316babb34
Source dataset
uspto-grants-2005_10
Patent number
US06951930B2

Reaction notes

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