Diethyl Ether → HCID 24721593, compound

HRID 1414026Notes

Reaction equation

HRID 1414026 reaction equation
S(Cl)([Cl:3])=O.Cl.[NH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=2)[NH:11][CH:10]=1.[CH2:21](OCC)C>CO>[ClH:3].[NH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 678542344666-59-5

Product 1

HCID 24721593HCID 24721593, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
45 °C

Procedure

Thionyl chloride (25 ml) was added to Analar methanol (84 ml) at 0° C. over a period of 1 hour under nitrogen. 3-(2-Aminoethyl)-1H-indole-5-carboxylic acid hydrochloride (2.5 g) in Analar methanol (35 ml) was added at 0° C. and the mixture was heated at reflux under nitrogen for 2.5 hour, cooled to ca. 45° C. and dry diethyl ether (200 ml) was added. The mixture was cooled and left overnight at 0° C. giving the title compound (1.9 g) as white microcrystals m.p. 265.5°-267° C. T.L.C. Silica, ethyl acetate:2-propanol:water:ammonia (25:15:8:2) Rf 0.46.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen for 2.5 hour
  3. temperatureThe mixture was cooled

Sources & evidence

ORD record
ord-66a782b3379b4beba11cd97eb2c72c5d
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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