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

HRID 737171

반응식

HRID 737171 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 702Ethanol용매

실험 절차

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−).

후처리

  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

출처 및 근거

ORD 기록
ord-bf1e3eb4baff409c84040f25d0325913
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595398B2

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