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

HRID 737171

反応式

HRID 737171 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 702Ethanol溶媒

実験手順

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−).

後処理

  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

出典と根拠

ORDレコード
ord-bf1e3eb4baff409c84040f25d0325913
出典データセット
uspto-grants-2009_09
特許番号
US07595398B2

関連ノート

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