Cyclohexanecarbonyl chloride → HCID 12915151, compound

HRID 620950Notes

Reaction equation

HRID 620950 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[CH2:6][CH:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2].[CH:19]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH:19]1([C:25]([NH:14][CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N+:1]([O-:3])=[O:2])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 12915145HCID 12915145, compound

Product 1

HCID 12915151HCID 12915151, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

Procedure

10.0 g of 2-nitro-α-phenylphenethylamine in 75 ml of toluene is added dropwise to a stirred, cooled solution of 14.4 ml of cyclohexylcarbonyl chloride in 75 ml of toluene and 25 ml of pyridine. After complete addition the mixture is stirred at room temperature for 2 hours. The mixture is allowed to stand overnight, after which the tan precipitate is collected and washed with 100 ml of ether. The precipitate is recrystallized from 350 ml of methanol to give yellow needles, mp 210°-212° C. of N-cyclohexanecarbonyl-2-nitro-α-phenylphenethylamine.

Workup

  1. additionAfter complete addition the mixture
  2. waitto stand overnight
  3. customafter which the tan precipitate is collected
  4. washwashed with 100 ml of ether
  5. customThe precipitate is recrystallized from 350 ml of methanol

Sources & evidence

ORD record
ord-ef70cd0fad79483aa396617d3941da5b
Source dataset
uspto-grants-1989_04
Patent number
US04822914

Reaction notes

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