Acetyl chloride → HCID 20270846, compound

HRID 484957Notes

Reaction equation

HRID 484957 reaction equation
CO[CH2:3][N:4]1[CH2:9][N:8]([N+:10]([O-:12])=[O:11])[CH2:7][N:6]([N+:13]([O-:15])=[O:14])[CH2:5]1.C([Cl:19])(=O)C.[C:20]([Br:23])(=O)C>>[Cl:19][CH2:3][N:4]1[CH2:9][N:8]([N+:10]([O-:12])=[O:11])[CH2:7][N:6]([N+:13]([O-:15])=[O:14])[CH2:5]1.[Br:23][CH2:20][N:4]1[CH2:5][N:6]([N+:13]([O-:15])=[O:14])[CH2:7][N:8]([N+:10]([O-:12])=[O:11])[CH2:9]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10482Acetyl bromideHCID 20270848HCID 20270848, compound

Product 2

HCID 20270846HCID 20270846, compoundHCID 20270847HCID 20270847, compound

Procedure

Dunning and Dunning (J.Chem.Soc., 2925(1950)) have reported that treatment of 1-methoxymethyl-3,5-dinitro-1,3,5-triazacyclohexane with acetyl chloride and acetyl bromide gave 1-chloromethyl-3,5-dinitro-1,3,5-triazacyclohexane and 1-bromomethyl-3,5-dinitro-1,3,5-triazacyclohexane, respectively. This chemistry was applied to the current work on the eight-membered ring derivatives. Treatment of (Compound 3) with acetyl bromide gave a quatitative yield of 1-bromomethyl-3,5,7-trinitro-1,3,5,7-tetrazacyclooctane (Compound 4). Attempts to convert Compound 4 to Compound 5 with sodium azide were unsuccessful. Thus, a novel method Eq. 2 was needed and invented for the conversion of Compound 4 to Compound 5. ##STR2##

Sources & evidence

ORD record
ord-d92390dcc24f4190a6722a03e9565265
Source dataset
uspto-grants-1985_08
Patent number
US04534895

Reaction notes

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