Chlorosulfonyl isocyanate → 4-Chloro-3-cyanomethyl-indole-1-carboxylic acid amide

HRID 489730Notes

Reaction equation

HRID 489730 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:11][C:12]#[N:13])=[CH:5][NH:6]2.ClC1C=CC=C2C=1C=CN2.ClS([N:28]=[C:29]=[O:30])(=O)=O>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:11][C:12]#[N:13])=[CH:5][N:6]2[C:29]([NH2:28])=[O:30]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 913454-ChloroindoleHCID 43006592-(4-chloro-1H-indol-3-yl)acetonitrile2×

Product 1

HCID 235890504-Chloro-3-cyanomethyl-indole-1-carboxylic acid amideYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The (4-chloro-1H-indol-3-yl)-acetonitrile used in step 1 was prepared from commercially obtained 4-chloro-1H-indole (Aldrich Chemical Co. Cat. No. 24,622-0) using the procedure of steps 4 and 5 of Example 1. To (4-chloro-1H-indol-3-yl)-acetonitrile (500 mg, 2.62 mmol) dissolved in anhydrous dichloromethane (10 mL) was added chlorosulfonyl isocyanate (0.92 mL, 10.50 mmol). After 1.5 hours, the reaction was filtered and the resulting solid was washed with dichloromethane. The solid was then dissolved in acetone and water (2.5 mL) was added. The reaction mixture was concentrated to dryness to yield 4-Chloro-3-cyanomethyl-indole-1-carboxylic acid amide as a pale pink solid (377 mg, 62%). 1H NMR (DMSO-d6) δ: 4.27 (br s, 2H), 7.28 (m, 2H), 7.78 (br s, 2H), 7.98 (s, 1H), 8.28 (m, 1H); M+233.

Workup

  1. filtrationthe reaction was filtered
  2. washthe resulting solid was washed with dichloromethane
  3. dissolutionThe solid was then dissolved in acetone
  4. additionwater (2.5 mL) was added
  5. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-9a6232b7bffd4d36b799857a3f6d7f52
Source dataset
uspto-grants-2005_12
Patent number
US06979696B2

Reaction notes

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