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

HRID 1027988Notes

Reaction equation

HRID 1027988 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.ClS([N:16]=[C:17]=O)(=O)=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:17]#[N:16])=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 766596-Methoxy-1H-indole

Product 1

HCID 534011976-Methoxy-1H-indole-3-carbonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-methoxy-1H-indole (100.0 g, 679.0 mmol) in DMF (560 mL) was cooled to −78° C. and treated with chlorosulfonyl isocyanate (71 mL, 815 mmol). After the addition the reaction mixture was stirred for 1 hour. The dark solution was poured into ice water (2 L) and the light brown solid was collected by filtration, washed with additional water and dried to afford 6-methoxy-1H-indole-3-carbonitrile as a light brown solid (104.8 g, 90%).

Workup

  1. additionAfter the addition the reaction mixture
  2. filtrationthe light brown solid was collected by filtration
  3. washwashed with additional water
  4. customdried

Sources & evidence

ORD record
ord-adb43c5e87e945b4aa93596e65c97812
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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