N-bromobutanimide → HCID 57758771, compound

HRID 1506922Notes

Reaction equation

HRID 1506922 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[S:11][CH:12]=[C:13]([CH3:20])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(Cl)(Cl)Cl>[NH2:9][C:10]1[S:11][C:12]([Br:1])=[C:13]([CH3:20])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylate

Product 1

HCID 57758771HCID 57758771, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-Bromosuccinimide (1.78 g) was added portion-wise to a solution of ethyl 2-amino-4-methylthiophene-3-carboxylate (1.71 g) in chloroform (25 ml) at 0° C. After 1 hour, the mixture was diluted with chloroform (20 ml) and washed with a mixture of brine and saturated aqueous sodium hydrogen carbonate (100 ml, 1:1). The organic phase was dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (0-20%) to give ethyl 2-amino-5-bromo-4-methylthiophene-3-carboxylate (1.32 g) as a bright yellow solid.

Workup

  1. washwashed with a mixture of brine and saturated aqueous sodium hydrogen carbonate (100 ml, 1:1)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane (0-20%)

Sources & evidence

ORD record
ord-3b30ae837aaa4ac095d0ad0ddb7bab0c
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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