Methyl chloroformate → Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamate

HRID 1667611Notes

Reaction equation

HRID 1667611 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].Cl[C:17]([O:19][CH3:20])=[O:18]>N1C=CC=CC=1>[C:7]([C:6]1[CH:9]=[C:2]([NH:1][C:17](=[O:18])[O:19][CH3:20])[CH:3]=[CH:4][C:5]=1[S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])#[N:8]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 574482075-Amino-2-(isopropylsulfonyl)benzonitrile

Product 1

HCID 57448208Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamateYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To 15C (450 mg, 2 mmol) in pyridine (10 mL) at 0° C. was added methyl chloroformate (0.8 mL, 10 mmol). The reaction was stirred at 0° C. for 20 min, then warmed to rt for 2 h. The reaction was concentrated, then diluted with ethyl acetate, washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes) to provide 15D (490 mg, 88%). LC-MS: 283.35 (M+H)+.

Workup

  1. temperaturewarmed to rt for 2 h
  2. concentrationThe reaction was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8b6db5b81d474600a0ed62124ad27042
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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