Triethylamine → HCID 53827968, compound

HRID 1863095Notes

Reaction equation

HRID 1863095 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]([C:8]1[NH:9][C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]2[C:16]=1[CH:15]=[CH:14][C:13]([Cl:17])=[CH:12]2)=[O:7].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]([C:8]1[NH:9][C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]2[C:16]=1[CH:15]=[CH:14][C:13]([Cl:17])=[CH:12]2)=[O:7])(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54314851HCID 54314851, compound

Product 1

HCID 53827968HCID 53827968, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 3.3 g. of 5-chloro-3-phenylisoindole-1-carboxylic acid 3-hydroxypropyl ester in a mixture of 60 ml. of methylene chloride and 5 ml. of triethylamine is treated dropwise at 15°-20° C. with a solution of 2.4 ml. of methanesulfonyl chloride in 10 ml. of methylene chloride and the mixture is stirred at room temperature for 1 hour. After dilution with 60 ml. of methylene chloride, the suspension is removed by filtration and the filtrate 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 a solid crude product which is chromatographed on 100 g. of silica gel using methylene chloride/ethyl acetate (4:1) for the elution. The uniform fractions yield 5-chloro-3-phenylisoindole-1-carboxylic acid 3-[(methylsulfonyl)oxy]propyl ester having a melting point of 155°-158° C. which can be used in the process without further purification. An analytical sample is obtained by recrystallization from ethanol, and there are obtained greenish crystals having a melting point of 159°-161° C.

Workup

  1. additionA suspension of 3.3 g
  2. customof methylene chloride, the suspension is removed by filtration
  3. washthe filtrate washed successively with water, 0.5-N hydrochloric acid, 5% sodium bicarbonate solution and again with water
  4. dry with materialAfter drying over sodium sulfate and evaporation of the solution
  5. customthere is obtained a solid crude product which
  6. customis chromatographed on 100 g
  7. washfor the elution

Sources & evidence

ORD record
ord-85c7fe16c1e64132a06e806728e13dbb
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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