N-bromobutanimide → 5-Bromo-4-(trifluoromethyl)-1,3-thiazol-2-amine

HRID 716620Notes

Reaction equation

HRID 716620 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1[N:4]=[C:5]([NH2:8])[S:6][CH:7]=1.[Br:11]N1C(=O)CCC1=O>C(O)(=O)C.C(#N)C.C(Cl)Cl>[Br:11][C:7]1[S:6][C:5]([NH2:8])=[N:4][C:3]=1[C:2]([F:10])([F:9])[F:1]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 12014172-Thiazolamine, 4-(trifluoromethyl)-

Product 1

HCID 157107015-Bromo-4-(trifluoromethyl)-1,3-thiazol-2-amine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-trifluoromethyl-thiazole-2-ylamine (0.2 g; 1.2 mmol) in acetic acid (0.14 mL) and acetonitrile (1.4 mL) at 0° C. was added N-bromosuccinimide (0.23 g, 1.3 mmol). The reaction mixture was warmed to room temperature over 17 h. The reaction was diluted with methylene chloride, washed with saturated NaHCO3, dried, filtered and concentrated under vacuum to give the crude product. The residue was purified by column chromatography eluting with ethyl acetate/hexanes 0 to 20% to give the product.

Workup

  1. washwashed with saturated NaHCO3
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4024146cb7cc457795f0ea8ab19405ad
Source dataset
uspto-grants-2015_11
Patent number
US09192603B2

Reaction notes

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