Ethanol → 2-(2,5-Dichloro-3-methanesulfonyl-indol-1-yl)-acetimidic acid ethyl ester hydrochloride

HRID 23401Notes

Reaction equation

HRID 23401 reaction equation
[Cl:1][C:2]1[N:3]([CH2:16][C:17]#[N:18])[C:4]2[C:9]([C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][C:7]([Cl:15])=[CH:6][CH:5]=2.[CH2:19]([OH:21])[CH3:20]>C(Cl)(Cl)Cl>[ClH:1].[CH2:19]([O:21][C:17](=[NH:18])[CH2:16][N:3]1[C:4]2[C:9](=[CH:8][C:7]([Cl:15])=[CH:6][CH:5]=2)[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[C:2]1[Cl:1])[CH3:20]

Participants

4

Reactant 2

HCID 702EthanolHCID 22574012(2,5-Dichloro-3-methylsulfonyl-indol-1-yl)-acetonitrile

Product 1

HCID 695462252-(2,5-Dichloro-3-methanesulfonyl-indol-1-yl)-acetimidic acid ethyl ester hydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (2,5-dichloro-3-methylsulfonyl-indol-1-yl)-acetonitrile (0.303 g, 1 mmole) in dry chloroform (15 ml) was cooled to 0° C. under a nitrogen atmosphere. To this solution was added anhydrous ethanol (0.35 ml). Dry hydrogen chloride gas was bubbled into the reaction mixture to saturation at 0° C. The flask was stoppered and stirred for 2 h at 0 and left in the freezer overnight. The resulting white solid precipitate was filtered off and dried to afford 0.353 g (91%) of 2-(2,5-dichloro-3-methanesulfonyl-indol-1-yl)-acetimidic acid ethyl ester hydrochloride.

Workup

  1. customDry hydrogen chloride gas was bubbled into the reaction mixture to saturation at 0° C
  2. waitleft in the freezer overnight
  3. filtrationThe resulting white solid precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-d94932f83a294bdbab27330a23d11799
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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