N-bromobutanimide → HCID 67125220, compound

HRID 1958084Notes

Reaction equation

HRID 1958084 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:11]=[C:10]([CH3:19])[N:9]=1.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:19][C:10]1[N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18981952Ethyl 4-(2-chlorophenyl)-2-methylpyrimidine-5-carboxylate

Product 1

HCID 67125220HCID 67125220, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

An amount of 820 mg (2.96 mmol) of ethyl 4-(2-chlorophenyl)-2-methylpyrimidine-5-carboxylate and 633 mg (3.55 mmol) of N-bromosuccinimide were dissolved in 18 ml of carbon tetrachloride and heated with stirring to boiling. At the heat of boiling, in portions, 49 mg (0.29 mmol) of 2,2′-azobis-2-methylpropanenitrile were added over 5 hours, followed by refluxing for a further hour. After cooling to room temperature, the reaction solution was filtered and the mother liquor was freed from the solvent under reduced pressure. The desired product was isolated by chromatographic purification.

Workup

  1. temperatureheated
  2. temperatureAt the heat
  3. additionwere added over 5 hours
  4. temperatureby refluxing for a further hour
  5. filtrationthe reaction solution was filtered

Sources & evidence

ORD record
ord-cc4bbd6aafed4497bed39242722ecd9e
Source dataset
uspto-grants-2013_04
Patent number
US08410106B2

Reaction notes

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