Dimethyl Sulfoxide → HCID 20140082, compound

HRID 1252488Notes

Reaction equation

HRID 1252488 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:14]=1.CS(C)=O.[OH-].[Na+].C(Cl)[Cl:31]>O>[ClH:31].[ClH:31].[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:23][CH2:22][CH2:21][CH2:20][CH2:19][C:15]1[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=1)=[O:4]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8359Isatoic AnhydrideHCID 14798Sodium HydroxideHCID 72927Pyridine, 3-(4-aminobutyl)-

Product 1

HCID 20140082HCID 20140082, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.25 g of isatoic anhydride, 3.0 g of 4-(3-pyridinyl)butylamine and 20 ml of dimethylsulfoxide was allowed to stand overnight at room temperature, then was treated with 40 ml of water, 10 ml of 1N sodium hydroxide and 200 ml of methylene chloride. The organic layer was separated, washed with water, dried over magnesium sulfate and concentrated. The oily residue was mixed with ethanolic hydrogen chloride and concentrated. The residue was triturated with ether to obtain the desired product, mp 220°-223° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. additionThe oily residue was mixed with ethanolic hydrogen chloride
  6. concentrationconcentrated
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-34a6e8ef1111441782abb8830fecb2e9
Source dataset
uspto-grants-1988_05
Patent number
US04743610

Reaction notes

Loading…