Acetyl chloride → 1-(Azidomethyl)-3,5,7-trinitro-1,3,5,7-tetrazocane

HRID 484958Notes

Reaction equation

HRID 484958 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C(Cl)(=O)C.Br[CH2:10][N:11]1[CH2:18][N:17]([N+:19]([O-:21])=[O:20])[CH2:16][N:15]([N+:22]([O-:24])=[O:23])[CH2:14][N:13]([N+:25]([O-:27])=[O:26])[CH2:12]1>O.C(Cl)Cl>[N:1]([CH2:10][N:11]1[CH2:18][N:17]([N+:19]([O-:21])=[O:20])[CH2:16][N:15]([N+:22]([O-:24])=[O:23])[CH2:14][N:13]([N+:25]([O-:27])=[O:26])[CH2:12]1)=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 33557Sodium AzideHCID 12841678HCID 12841678, compound

Product 1

HCID 130222381-(Azidomethyl)-3,5,7-trinitro-1,3,5,7-tetrazocane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of sodium azide (345 g, 5.45 mole) in water (1200 mL) was cooled to 5° C. and with good stirring a solution of acetyl chloride (286 g, 3.64 mol) in methylene chloride (640 mL) was added in 2.5 h, maintaining the temperature at 5° C. with external cooling. The upper aqueous layer was siphoned off and Compound 4 (101 g, 0.294 mol) was added. The mixture was stirred for 3 h at 10°-15° C. and filtered. The white solid was washed with methylene chloride (2×200 mL), water (200 mL), and ether (2×200 mL), and dried in a vacuum oven overnight at 40° C. The yield of Compound 5 was 71 g (79%), m.p. 130°-131° C. IR (KBr) 2080 cm-1 (N3), 1540 cm-1 (N--NO2). HPLC analysis showed a single peak. Analysis calculated for C5H10N10O6 : C,19.61: H,3.27; N,45.75. Found: C,19.99: H,3.28; N,44.99.

Workup

  1. additionwas added in 2.5 h
  2. filtrationfiltered
  3. washThe white solid was washed with methylene chloride (2×200 mL), water (200 mL), and ether (2×200 mL)
  4. customdried in a vacuum oven overnight at 40° C

Sources & evidence

ORD record
ord-d5b401ef47934896817a8d4684f67a6a
Source dataset
uspto-grants-1985_08
Patent number
US04534895

Reaction notes

Loading…