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

HRID 252479Notes

Reaction equation

HRID 252479 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 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-methoxyindole (10.0 g, 68.0 mmol) in DMF (120 mL) is cooled to 0° C. and treated with chlorosulfonyl isocyanate (7.72 mL, 88.4 mmol). After the addition, the reaction mixture is stirred at this temperature for 1 h. The dark solution is poured into ice water (600 mL) and the light brown solid is collected by filtration, washed with additional H2O and dried to afford 9.9 g (85%) of 6-methoxy-1H-indole-3-carbonitrile as a light brown solid.

Workup

  1. additionAfter the addition
  2. filtrationthe light brown solid is collected by filtration
  3. washwashed with additional H2O
  4. customdried

Sources & evidence

ORD record
ord-26b5173d25d64fd7b513b24f4cd945be
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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