N-bromobutanimide → HCID 67125220, compound

HRID 874184Notes

Reaction equation

HRID 874184 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

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, with stirring, heated to the boil. At boiling point, 49 mg (0.29 mmol) of 2,2′-azobis-2-methylpropionitrile were added a little at a time over a period of 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 to the boil
  2. additionwere added a little at a time over a period of 5 hours
  3. temperatureby refluxing for a further hour
  4. filtrationthe reaction solution was filtered

Sources & evidence

ORD record
ord-f560c7d869f14d1fb147ae7209bc58bf
Source dataset
uspto-grants-2015_03
Patent number
US08980886B2

Reaction notes

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