Triethylamine → 3-(1-Methyl-2-chloro-3-indolyl)-2-methylsulfonylacrylonitrile

HRID 1957230Notes

Reaction equation

HRID 1957230 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[C:3]1[Cl:13].[CH3:14][S:15]([CH2:18][C:19]#[N:20])(=[O:17])=[O:16].C(N(CC)CC)C>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[C:18]([S:15]([CH3:14])(=[O:17])=[O:16])[C:19]#[N:20])=[C:3]1[Cl:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75283(Methylsulfonyl)acetonitrile2×HCID 3147922-Chloro-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 539397503-(1-Methyl-2-chloro-3-indolyl)-2-methylsulfonylacrylonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 550 mg of 1-methyl-2-chloroindole-3-carbaldehyde, dissolved in 25 ml of THF, was added 730 mg of methylsulfonylacetonitril and 1.2 g of triethylamine. After 24 hours another 300 mg of methylsulfonylacetonitril was added, and the mixture was stirred for 6 days. The precipitate was collected by filtration to give (3a). Yield 630 mg of (3a), m.p. 180° C.

Workup

  1. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9eb0e228c0f0488a9229d57f92509cc7
Source dataset
uspto-grants-1998_07
Patent number
US05783575

Reaction notes

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