N-methyl-2-pyrrolidone → HCID 21460403, compound

HRID 1941214Notes

Reaction equation

HRID 1941214 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:17])[C:13](Br)([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].CN1CCCC1=O>O>[N:18]([C:13]([CH3:15])([CH3:14])[C:12]([NH:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:17])=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 33557Sodium AzideHCID 21460400HCID 21460400, compound

Product 1

HCID 21460403HCID 21460403, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the crude amide (104 g), sodium azide (23.6 g) and N-methyl-2-pyrrolidone (500 ml) was heated at 50° C. for 22 h. After cooling to room temperatur water was added and the resulting mixture was extracted with diethyl ether (2×400 ml). The combined organic phases were washed with brine (3×500 ml) and dried (Na2 SO4). Evaporation of the solvents in vacuo gave 2-azido-N-(2-benzyloxyethyl)-2-methylpropionamide as an oil:78 g.

Workup

  1. additionwas added
  2. extractionthe resulting mixture was extracted with diethyl ether (2×400 ml)
  3. washThe combined organic phases were washed with brine (3×500 ml)
  4. customdried (Na2 SO4)
  5. customEvaporation of the solvents in vacuo

Sources & evidence

ORD record
ord-99b54387901841e48c5c9d37684377d8
Source dataset
uspto-grants-1997_12
Patent number
US05703087

Reaction notes

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