Triethylamine → Sulpiride

HRID 1759508Notes

Reaction equation

HRID 1759508 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH2:16]([N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][NH2:24])[CH3:17].C1C(=O)N(OP(OC2C=CC=CC=2)(OC2C=CC=CC=2)=O)C(=O)C1.C(N(CC)CC)C>C(#N)C>[CH3:17][CH2:16][N:18]1[CH:19]([CH2:23][NH:24][C:5]([C:4]2[CH:8]=[C:9]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:10]=[CH:11][C:3]=2[O:2][CH3:1])=[O:7])[CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 896012-Methoxy-5-sulfamoylbenzoic acidHCID 43863971-[(Diphenoxyphosphoryl)oxy]pyrrolidine-2,5-dioneHCID 19022581HCID 19022581, compound

Product 1

HCID 5355SulpirideYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 462 mg (0.002 mol) of 2-methoxy-5-aminosulfonylbenzoic acid and 256 mg (0.002 mol) of N-ethyl-2-aminomethylpyrrole in 10 ml of acetonitrile was admixed with 694 mg (0.002 mol) of SDPP and 202 mg (0.002 mol) of triethylamine, and the admixture was stirred overnight at room temperature. The crystalline material deposited was collected by filtration and washed with acetonitrile and then with ethanol to give sulpiride, that is, 5-(aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl) methyl]-2-methoxybenzamide. mp. 182°~185° C. Yield 24%.

Workup

  1. filtrationThe crystalline material deposited was collected by filtration
  2. washwashed with acetonitrile

Sources & evidence

ORD record
ord-4034eb5a7ee14249a207b483a594b888
Source dataset
uspto-grants-1982_07
Patent number
US04341707

Reaction notes

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