Sodium Azide → HCID 14153831, compound

HRID 1253005Notes

Reaction equation

HRID 1253005 reaction equation
Cl[CH2:2][C:3](=[O:18])[CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1)[CH2:6][CH3:7].[N-:19]=[N+:20]=[N-:21].[Na+]>CO>[N:19]([CH2:2][C:3](=[O:18])[CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1)[CH2:6][CH3:7])=[N+:20]=[N-:21]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 14153828HCID 14153828, compound

Product 1

HCID 14153831HCID 14153831, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the chloromethyl ketone (7, 5.9 g, 0.022 mol), 10.8 g (0.16 mol) of NaN3 and 180 ml of 80% MeOH was stirred at room temperature for 20 hours. After evaporation of MeOH the aqueous residue was diluted to 100 ml with H2O and extracted with three 50 ml portions of CHCl3. The CHCl3 was dried (MgSO4) and evaporated to leave 5.5 g (91%) of a yellow oil (8); TLC (silica gel, CHCl3 0C6H6, 1:1) Rf 0.30 single spot; IR cm-1 2105 (--N3); NMR (CDCl3) δ 0.80 (3H, t, CH3), 1.70 (2H, m, CH2CH3), 2.80 (2H, m, CH2C=O), 3.15 (1H, m, Ar--CH), 3.77 (2H, s, CH2N3), 3.90 (3H, s, OCH3), 7.30 (2H, d, 3', 5'--ArH), 8.05 (2H, d, 2', 6'--ArH).

Workup

  1. customAfter evaporation of MeOH the aqueous residue
  2. additionwas diluted to 100 ml with H2O
  3. extractionextracted with three 50 ml portions of CHCl3
  4. dry with materialThe CHCl3 was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-2973c305d8c84be5af55021349cbf820
Source dataset
uspto-grants-1988_05
Patent number
US04746659

Reaction notes

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