Dicyclohexylcarbodiimide → N-(3-amino-5-nitrophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide

HRID 261362Notes

Reaction equation

HRID 261362 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][CH:5]([C:7]([OH:9])=O)[CH2:4][O:3]1.[NH2:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[C:16]([NH2:18])[CH:17]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>[NH2:18][C:16]1[CH:17]=[C:12]([NH:11][C:7]([CH:5]2[CH2:4][O:3][C:2]([CH3:1])([CH3:10])[O:6]2)=[O:9])[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=1

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 211345-Nitro-1,3-benzenediamineHCID 109096992,2-Dimethyl-1,3-dioxolane-4-carboxylic acid

Product 1

HCID 20394921N-(3-amino-5-nitrophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamideYield 68.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.5 g (2.9 mmole) of 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid in 2 ml of methylene chloride, at 0° C., was added a solution of 0.216 g of 3,5-diaminonitrobenzene (1.3 mmole) in 2 ml of methylene chloride and 1 ml of pyridine, followed by 0.61 g (3.0 mmole) of dicyclohexylcarbodiimide. The mixture was stirred 72 hours, diluted with ethyl acetate, filtered and the filtrate evaporated to dryness in high vacuum. The residue was chromatographed over silica gel; elution with 9:1 chloroform-ethyl acetate gave two fractions. The first fraction, 170 mg was the bis-acylated material. The second fraction was evaporated to dryness to give 250 mg of N-(3-amino-5-nitrophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness in high vacuum
  3. customThe residue was chromatographed over silica gel
  4. washelution with 9:1 chloroform-ethyl acetate
  5. customgave two fractions
  6. customThe second fraction was evaporated to dryness

Sources & evidence

ORD record
ord-c533fb731dcc47ea86f6bed52c6e97b8
Source dataset
uspto-grants-1979_08
Patent number
US04165365

Reaction notes

Loading…