Hydrochloric Acid → N-[4-Chloro-5-(2-chloro-2-ethoxycarbonyleth-1-yl)-2-fluorophenyl]-3,4,5,6-tetrahydrophthalimide

HRID 398805Notes

Reaction equation

HRID 398805 reaction equation
N[C:2]1[C:3]([Cl:20])=[CH:4][C:5]([F:19])=[C:6]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])[CH:7]=1.N(OC(C)(C)C)=O.[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=[CH2:30].[ClH:35]>C(#N)C.[Cu](Cl)Cl>[Cl:20][C:3]1[C:2]([CH2:30][CH:29]([Cl:35])[C:28]([O:32][CH2:33][CH3:34])=[O:31])=[CH:7][C:6]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[C:5]([F:19])[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 10906Tert-Butyl nitriteHCID 15590180N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 22013643N-[4-Chloro-5-(2-chloro-2-ethoxycarbonyleth-1-yl)-2-fluorophenyl]-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

3.5 g of N-(5-amino-4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide in 5 ml of absolute acetonitrile were added dropwise to a suspension of 1.9 g of tert-butyl nitrite, 260 g of ethyl acrylate and 1.9 g of anhydrous copper(II) chloride in 200 ml of absolute acetonitrile at 0° C. The mixture was slowly warmed up to room temperature and was stirred at this temperature for 10 hours. 40 ml of dilute hydrochloric acid were then added, and the mixture was extracted three times with methyl tert-butyl ether. The combined organic phases were dried over sodium sulfate and evaporated down. The residue was chromatographed over silica gel (eluent: 2:1 petroleum ether/diethyl ether).

Workup

  1. extractionthe mixture was extracted three times with methyl tert-butyl ether
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated down
  4. customThe residue was chromatographed over silica gel (eluent: 2:1 petroleum ether/diethyl ether)

Sources & evidence

ORD record
ord-5dc31e3f05c64cbbb277b58216649340
Source dataset
uspto-grants-1998_10
Patent number
US05817603

Reaction notes

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