3,4-dinitrobenzoyl Chloride → HCID 54275678, compound

HRID 1861717Notes

Reaction equation

HRID 1861717 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH2:15])=[CH:5][C:4]=1[O:16][CH3:17].[N+:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[N+:30]([O-:32])=[O:31])[C:24](Cl)=[O:25])([O-:20])=[O:19]>C(Cl)Cl.C(N(CC)CC)C>[CH3:17][O:16][C:4]1[CH:5]=[C:6]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:29]([N+:30]([O-:32])=[O:31])=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 118064913,4-dinitrobenzoyl ChlorideHCID 14321190(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene2×

Product 1

HCID 54275678HCID 54275678, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

5.0 g of (−)-cis-1,2-dimethoxy-4-(2-aminocyclohexyl)benzene (compound B2) are dissolved in 40 ml of methylene chloride and 5.0 ml of triethylamine. A solution of 6.5 g of 3,4-dinitrobenzoyl chloride in 40 ml of methylene chloride is added dropwise at RT and the mixture is extracted with water, 2N hydrochloric acid, satd. sodium hydrogencarbonate solution and water again after stirring overnight. The organic phase is dried using sodium sulfate and concentrated. 8.1 g of the title compound are obtained as a solidified oil.

Workup

  1. extractionthe mixture is extracted with water, 2N hydrochloric acid
  2. customThe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7b0857de6d7441f89b4c066987667095
Source dataset
uspto-grants-2003_03
Patent number
US06534518B1

Reaction notes

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