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

HRID 502283Notes

Reaction equation

HRID 502283 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>CN(C=O)C>[C:18]([C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[NH:10][CH:9]=1)#[N:17]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 785026-Nitro-1H-indole

Product 1

HCID 2831796-Nitro-1H-indole-3-carbonitrileYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-nitroindole (16.2 g, 100 mmol) in DMF (60 mL) at 0° C. was added chlorosulfonylisocyanate (10.9 mL, 125.0 mmol). The mixture was then stirred at room temperature overnight, poured into ice-water (1.0 L) and stirred for 3 h. The precipitate was filtered, washed with water and dried in air to provide 3-cyano-6-nitroindole (17.63 g, 94%).

Workup

  1. stirringstirred for 3 h
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried in air

Sources & evidence

ORD record
ord-841a98ce13ec442e9dc8b2e576d42949
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

Loading…