Cyclohexylamine → HCID 711421, compound

HRID 2228954Notes

Reaction equation

HRID 2228954 reaction equation
ClC(OCC(C)C)=O.[Cl:9][C:10]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:11]=1[C:12]([OH:14])=O.C(N(CC)CC)C.[CH:29]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH:29]1([NH:35][C:12](=[O:14])[C:11]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:10]=2[Cl:9])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 172872-Chloro-5-nitrobenzoic acidHCID 62365Isobutyl chloroformate

Product 1

HCID 711421HCID 711421, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Isobutyl chloroformate (1.43 ml) was added under ice cooling to a solution of 2-chloro-5-nitrobenzoic acid (2.01 g) and triethylamine (1.53 ml) in methylene chloride (40 ml). The mixture was stirred under ice cooling for 45 min. Thereafter, cyclohexylamine (1.25 ml) was added thereto. The reaction solution was stirred at room temperature for 1.5 hr. The precipitated crystals were dissolved in chloroform. The organic layer was washed with water, dilute hydrochloric acid, and water in that order, dried over magnesium sulfate, and then concentrated under the reduced pressure. Ethyl ether was added to the residue. The precipitated crystals were collected by filtration, and then dried to give 2.63 g of N-cyclohexyl-2-chloro-5-nitrobenzamide.

Workup

  1. stirringThe reaction solution was stirred at room temperature for 1.5 hr
  2. washThe organic layer was washed with water, dilute hydrochloric acid, and water in that order
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under the reduced pressure
  5. additionEthyl ether was added to the residue
  6. filtrationThe precipitated crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-23333268edfb465b99aedfff5c9cdc78
Source dataset
uspto-grants-2002_07
Patent number
US06417362B1

Reaction notes

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