Triethylamine → 5-Chloro-2-{2-[(methylsulfonyl)oxy]ethyl}-3-phenylisoindole-1-carboxylic acid ethyl ester

HRID 372317Notes

Reaction equation

HRID 372317 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][OH:24])[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2].C(N(CC)CC)C.[S:32](Cl)([OH:35])(=O)=[O:33].[CH4:37]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][O:24][S:32]([CH3:37])(=[O:35])=[O:33])[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19821184Methane sulfochlorideHCID 544328935-Chloro-2-(2-hydroxyethyl)-3-phenylisoindole-1-carboxylic acid ethyl ester

Product 1

HCID 536910545-Chloro-2-{2-[(methylsulfonyl)oxy]ethyl}-3-phenylisoindole-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.4 g. of 5-chloro-2-(2-hydroxyethyl)-3-phenylisoindole-1-carboxylic acid ethyl ester and 3.4 ml. of triethylamine in 60 ml. of methylene chloride is treated dropwise at 15°-20° C. with 1.6 ml. of methane sulfochloride. The mixture is subsequently left standing for 30 minutes at room temperature, then diluted with methylene chloride to three times the volume. The solution is washed successively with water, 0.5-N hydrochloric acid, 5% sodium bicarbonate solution and again with water. After drying over sodium sulfate and evaporation of the solution, there is obtained 5-chloro-2-{2-[(methylsulfonyl)oxy]ethyl}-3-phenylisoindole-1-carboxylic acid ethyl ester; melting point 125°-127° C. Recrystallization from methylene chloride/hexane does not increase the melting point.

Workup

  1. waitThe mixture is subsequently left
  2. washThe solution is washed successively with water, 0.5-N hydrochloric acid, 5% sodium bicarbonate solution and again with water
  3. dry with materialAfter drying over sodium sulfate and evaporation of the solution

Sources & evidence

ORD record
ord-db1820a573754e098a23605a7b8b537c
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

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