4-Acetylbenzoic Acid → 4-(2-Amino-1,3-thiazol-4-yl)benzoic acid

HRID 737168

Reaction equation

HRID 737168 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=O)[CH3:2].BrBr.BrC(Br)=O.CC([O-])=O.[Na+].[NH2:24][C:25]([NH2:27])=[S:26]>CC(O)=O.C(O)C>[NH2:27][C:25]1[S:26][CH:2]=[C:1]([C:4]2[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=2)[N:24]=1

Participants

8

Reactant 5

HCID 114704-Acetylbenzoic AcidHCID 24408BromineHCID 79057Carbonyl bromideHCID 517045Sodium AcetateHCID 2723790Thiourea

Product 1

HCID 6131794-(2-Amino-1,3-thiazol-4-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 4-acetyl-benzoic acid (10 g, 61 mmol), in HOAc (400 mL) at 55° C. was treated with bromine (1 eq., 3.12 mL) dropwise over 10 minutes. After 90 minutes the reaction was cooled, the acetic acid was removed, ethyl acetate (50 mL) was added and then removed to get rid of the remainder of the acetic acid. The crude bromo ketone was then dissolved in ethanol (200 mL) with NaOAc (12 g) and thiourea (1 eq. 4.4 g) was added. The suspension was stirred at room temperature for 15 hours. The solvents were removed and the solids washed with water (3×100 mL) then ether:ethanol (4:1, 3×100 mL) and dried to give the product as a tan solid. MS: 221.2 (M+H+).

Workup

  1. temperatureAfter 90 minutes the reaction was cooled
  2. customthe acetic acid was removed
  3. additionethyl acetate (50 mL) was added
  4. customremoved
  5. customto get rid of the remainder of the acetic acid
  6. additionwas added
  7. customThe solvents were removed
  8. washthe solids washed with water (3×100 mL)
  9. dry with materialether:ethanol (4:1, 3×100 mL) and dried

Sources & evidence

ORD record
ord-d29e033db8d04bd3b35694af9be5cf39
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Linked notes

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