1-Chloro-2-nitrobenzene → HCID 21510668, compound

HRID 1576477Notes

Reaction equation

HRID 1576477 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[NH:6][C:5](=[O:17])[CH2:4][C:3]1=[O:18].C([O-])(=O)C.[K+].Cl[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N+:31]([O-:33])=[O:32]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:14])[F:15])=[CH:12][C:7]=2[N:6]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])[C:5](=[O:17])[CH2:4][C:3]1=[O:18]

Participants

6

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 517044Potassium AcetateHCID 215106781-Methyl-7-(trifluoromethyl)-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 21510668HCID 21510668, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

26 gm. (0.1 mol) of 1-methyl-7-trifluoromethyl-1,5-benzodiazepine-2,4-(3H,5H)-dione were heated with 13 gm. of potassium acetate, 1 gm. of anhydrous copper sulfate and 350 gm. of o-chloro-nitrobenzene for one hour at 150°C. The reaction solution was diluted with methylene chloride, washed with dilute ammonia, sodium hydroxide solution and water, the organic phase was dried, and the solvent evaporated in vacuo. The residue was carefully admixed with petroleum ether, whereby a precipitate was formed, which was recrystallized from methylene chloride/isopropylether. Yield: 30 gm. (80% of theory) of the compound of the formula ##SPC9##

Workup

  1. washwashed with dilute ammonia, sodium hydroxide solution and water
  2. customthe organic phase was dried
  3. customthe solvent evaporated in vacuo
  4. customwas formed
  5. customwhich was recrystallized from methylene chloride/isopropylether

Sources & evidence

ORD record
ord-bc6c3d95a244449783e6cfec5997427f
Source dataset
uspto-grants-1976_09
Patent number
USRE028972

Reaction notes

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