N-bromobutanimide → 2-Bromomethyl-5-ethoxycarbonyl-4-methylthiazole

HRID 434656Notes

Reaction equation

HRID 434656 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:11][C:9]1[S:10][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:7]([CH3:12])[N:8]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 603810Ethyl 2,4-dimethylthiazole-5-carboxylate

Product 1

HCID 204917652-Bromomethyl-5-ethoxycarbonyl-4-methylthiazoleYield 41.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-ethoxycarbonyl-2,4-dimethylthiazole (926 mg), N-bromosuccinimide (890 mg) and benzoyl peroxide (8 mg) in carbon tetrachloride (11 ml) was heated at reflux. After 11/2 h the reaction mixture was allowed to cool and filtered. The filtrate was evaporated and the residual oil diluted with petrol (b.p. 40°-60° C.)-ethyl acetate, 4:1, (5 ml) resulting in the precipitation of a solid. After 1 h the suspension was filtered and the filtrate evaporated to an orange oil. Petrol (2 ml) was added to the oil resulting in the formation of a solid which after cooling was collected to give crystals of 2-bromomethyl-5-ethoxycarbonyl-4-methylthiazole (546 mg), m.p. 48°-58° C., λmax (EtOH) 266 nm (ε 8,640).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. custom2 h
  4. temperatureto cool
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. additionthe residual oil diluted with petrol (b.p. 40°-60° C.)-ethyl acetate, 4:1, (5 ml)
  8. customresulting in the precipitation of a solid
  9. filtrationAfter 1 h the suspension was filtered
  10. customthe filtrate evaporated to an orange oil
  11. additionPetrol (2 ml) was added to the oil
  12. customresulting in the formation of a solid which
  13. temperatureafter cooling
  14. customwas collected

Sources & evidence

ORD record
ord-9fbfb7768bcc4209858faffdcb0ef5a1
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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