1,4-Diacetylbenzene → 1-[4-(2-Amino-thiazol-4-yl)-phenyl]-ethanone

HRID 737171Notes

Reaction equation

HRID 737171 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[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:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=2)[N:24]=1

Participants

8

Reactant 5

HCID 138881,4-DiacetylbenzeneHCID 24408BromineHCID 79057Carbonyl bromideHCID 517045Sodium AcetateHCID 2723790Thiourea

Product 1

HCID 866164311-[4-(2-Amino-thiazol-4-yl)-phenyl]-ethanone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent

Procedure

A solution of 1-(4-Acetyl-phenyl)-ethanone (8.1 g, 5 mmol), in HOAc (50 mL) at 60° C. was treated with bromine (1 eq., 0.26 mL) dropwise over 10 minutes. After 5 more minutes the reaction was cooled, the acetic acid was removed, ethyl acetate (50 mL) was added and then removed to get drive off the remainder of the acetic acid. The crude bromo ketone was then dissolved in ethanol (30 mL) with NaOAc (1.1 g) and thiourea (1 eq., 375 mg) was added. The suspension was stirred at room temperature for 15 hours. The solvents were removed and the resulting mixture was redissolved in 5 ml of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product. MS: 219.1 (M+H−).

Workup

  1. temperatureAfter 5 more minutes the reaction was cooled
  2. customthe acetic acid was removed
  3. additionethyl acetate (50 mL) was added
  4. customremoved
  5. customto get
  6. additionwas added
  7. customThe solvents were removed
  8. dissolutionthe resulting mixture was redissolved in 5 ml of 90% DMF
  9. custom10% water with 0.1% TFA and purified by reverse phase HPLC
  10. customto give the product

Sources & evidence

ORD record
ord-bf1e3eb4baff409c84040f25d0325913
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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