Chlorosulfonyl isocyanate → 6-Nitro-1H-indole-3-carbonitrile

HRID 1908473Notes

Reaction equation

HRID 1908473 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].ClS([N:17]=[C:18]=O)(=O)=O.C([O-])(O)=O.[Na+]>CN(C=O)C.CC#N>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:18]#[N:17])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 785026-Nitro-1H-indoleHCID 516892Sodium Bicarbonate

Product 1

HCID 2831796-Nitro-1H-indole-3-carbonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 6-nitroindole (4.9 g 30 mmol) in DMF (24 mL) and CH3CN (240 mL) was added dropwise a solution of ClSO2NCO (5.0 mL) in CH3CN (39 mL) at 0° C. After addition, the reaction was allowed to warm to room temperature and was stirred for 2 h. The mixture was then poured into ice-water and basified with sat. NaHCO3 solution to pH 7˜8. The mixture was extracted with ethyl acetate. The organics were washed with brine, dried over Na2SO4 and concentrated to give 6-nitro-1H-indole-3-carbonitrile (4.6 g, 82%).

Workup

  1. additionAfter addition
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-32aed6e58dc54234aa37d8194e92c11b
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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