Bromine → 2-Amino-5-bromo-1,3-thiazole-4-carbonitrile

HRID 661044Notes

Reaction equation

HRID 661044 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]#[N:8])[N:6]=1.[Br:9]Br>CC(O)=O>[NH2:1][C:2]1[S:3][C:4]([Br:9])=[C:5]([C:7]#[N:8])[N:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 50841832-Amino-4-cyanothiazole

Product 1

HCID 576340092-Amino-5-bromo-1,3-thiazole-4-carbonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Aminothiazole-4-carbonitrile (1.40 g, 11.18 mmol) was dissolved in 20 mL AcOH in a 150 mL round bottom flask. Br2 (1.78 g, 11.18 mmol) was added to the reaction in a dropwise manner. After stirring at room temperature for 10 minutes, AcOH was removed under vacuum. Saturated sodium bicarbonate was added to the reaction mixture, and the mixture was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine and dried over sodium sulfate. 2-amino-5-bromothiazole-4-carbonitrile (1.20 g, yield: 53%) was obtained. LCMS (API-ES) m/z (%): 205.9 (100%, M++2H).

Workup

  1. customAcOH was removed under vacuum
  2. additionSaturated sodium bicarbonate was added to the reaction mixture
  3. extractionthe mixture was extracted with EtOAc (2×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-62276670cd1a432784189f999ae6416b
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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