Dimethylformamide → 1,3,5-Trichloro-2,4,6-trinitrobenzene

HRID 358927

Reaction equation

HRID 358927 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[C:12]([N+:26]([O-:28])=[O:27])=[C:13](OC)[C:14]([N+:21]([O-:23])=[O:22])=[C:15]([Cl:20])[C:16]=1[N+:17]([O-:19])=[O:18]>C1(C)C=CC=CC=1>[Cl:10][C:11]1[C:12]([N+:26]([O-:28])=[O:27])=[C:13]([Cl:3])[C:14]([N+:21]([O-:23])=[O:22])=[C:15]([Cl:20])[C:16]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 147940571,3-Dichloro-5-methoxy-2,4,6-trinitrobenzene

Product 1

HCID 175181,3,5-Trichloro-2,4,6-trinitrobenzeneYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

Thionyl chloride (0.20 ml, 0.027 mol) and dimethylformamide (0.15 ml, 0.022 mol) were added to a solution of 5 (0.624 g, 0.020 mol) in toluene (2 ml) at 50° C. The mixture was stirred and heated to 95° C. over a period of 15 min. and maintained at that temperature for another hour. The pale yellow solution was washed with water, dried over magnesium sulfate, treated with activated carbon, filtered, and evaporated to give a cream-colored solid (0.600 g, 95% yield). The melting point of the material so obtained was 194-195° C. (195-196° C. after recrystallization from acetic acid).

Workup

  1. temperaturemaintained at that temperature for another hour
  2. washThe pale yellow solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with activated carbon
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6fd7ed6bceeb475aa404fdac8da39a05
Source dataset
uspto-grants-1991_03
Patent number
US04997987

Linked notes

Loading…