Ethyl Acetate → HCID 57587931、化合物

HRID 1782159ノート

反応式

HRID 1782159 の反応式
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[S:15][N:16]=[C:17]([CH3:18])[C:11]=2[N:10]=[C:9]1[CH2:19][CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:27]Br.CCOC(C)=O>C(O)(=O)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[S:15][N:16]=[C:17]([CH3:18])[C:11]=2[N:10]=[C:9]1[CH:19]([Br:27])[CH2:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 24408Bromine2 回HCID 517045Sodium AcetateHCID 54757216HCID 54757216、化合物

生成物 1

HCID 57587931HCID 57587931、化合物

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

To a solution of 6-benzyl-3-methyl-5-propyl-6H-isothiazolo[4,5-d]pyrimidin-7-one (method 59) (208 mg, 0.69 mmol) and sodium acetate (0.5 g, 5 mmol) in acetic acid (10 mL) at 100° C., a solution of the bromine (0.232 g, 1.46 mmol) in acetic acid (20 mL) was added dropwise [The next drop of Bromine was added only after the previous drop had reacted completely by monitoring the decolorization] over a period of 30 min. The reaction mixture was cooled after the addition and the TLC (eluent 10% EtOAc in hexanes) and MS showed the complete disappearance of the SM and only the product. The reaction mixture was poured into ice water and extracted with EtOAc (3×30 mL) and the organic layers were combined and washed with 2% sodium thiosulfate solution (30 mL), water (50 mL), brine (50 mL) and dried (Na2SO4). Concentration of the organic layer provided the product and it was pure enough to be used in the next step. Yield 260 mg (99%). 1H NMR (300 MHz) δ 0.77 (t, 3H), 2.20-2.54 (m, 2H), 2.70 (s, 3H), 4.67 (t, 1H), 4.95 (d, 1H), 6.25 (d, 1H) 7.10-7.19 (m, 2H), 7.30-7.39 (m, 3H).

後処理

  1. additionwas added only after the previous drop
  2. customhad reacted completely
  3. customof 30 min
  4. temperatureThe reaction mixture was cooled
  5. additionafter the addition
  6. extractionextracted with EtOAc (3×30 mL)
  7. washwashed with 2% sodium thiosulfate solution (30 mL), water (50 mL), brine (50 mL)
  8. dry with materialdried (Na2SO4)
  9. customConcentration of the organic layer provided the product and it

出典と根拠

ORDレコード
ord-b91fbfc67a7046248cef5aad38afdbce
出典データセット
uspto-grants-2009_03
特許番号
US07498333B2

反応ノート

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