Hydrochloric Acid → HCID 13770878, compound

HRID 1252602Notes

Reaction equation

HRID 1252602 reaction equation
Cl.Cl[CH2:3][C:4]1[NH:5][CH:6]=[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8](=[O:10])[CH:9]=1.[N-:19]=[N+:20]=[N-:21].[Na+].C(N(C(C)C)CC)(C)C.Cl>CN(C)C=O.O>[N:19]([CH2:3][C:4]1[NH:5][CH:6]=[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8](=[O:10])[CH:9]=1)=[N+:20]=[N-:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium Azide2×HCID 81531DiisopropylethylamineHCID 13770877HCID 13770877, compound

Product 1

HCID 13770878HCID 13770878, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(chloromethyl)-5-(phenylmethoxy)-4(1H)-pyridinone, monohydrochloride (3.59 g, 12.54 mmole), sodium azide (4.08 g, 62.7 mmole) and diisopropylethylamine (2.19 ml, 12.54 mmole) in 70 ml of dimethylformamide was stirred at room temperature under argon for 3.5 days. An additional 4.08 g of sodium azide was added and the mixture was heated at 45°-50° C. for 2 hours. After cooling, the reaction mixture was poured into 500 ml of water, producing an insoluble white solid. The pH of the supernatant liquid was lowered from 8.5 to 7.5 with dilute hydrochloric acid, and the white solid was filtered. After washing with water, acetone, and hexane the solid was dried in vacuo. The yield of the title compound was 2.81 g.

Workup

  1. temperaturethe mixture was heated at 45°-50° C. for 2 hours
  2. temperatureAfter cooling
  3. customproducing an insoluble white solid
  4. filtrationthe white solid was filtered
  5. washAfter washing with water, acetone, and hexane the solid
  6. customwas dried in vacuo

Sources & evidence

ORD record
ord-5d6e47cc1d5c4ae1992b6ed40e821589
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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