Phenothiazine → Tert-butyl 3-(phenothiazin-10-ylmethyl)benzoate

HRID 249165ノート

反応式

HRID 249165 の反応式
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]([CH3:19])([O-:18])[CH3:17].[K+].Cl[CH2:22][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[C:26](OC)=[O:27]>O1CCCC1>[CH:11]1[C:12]2[N:13]([CH2:22][C:23]3[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=3)[C:26]([O:18][C:16]([CH3:19])([CH3:17])[CH3:15])=[O:27])[C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[S:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 7108PhenothiazineHCID 3248988Methyl 3-(chloromethyl)benzoateHCID 23665647Potassium tert-butoxide2 回

生成物 1

HCID 19024810Tert-butyl 3-(phenothiazin-10-ylmethyl)benzoate収率 30.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of phenothiazine (1.00 g) in tetrahydrofuran (10 ml) was added potassium tert-butoxide (617 mg) at 0° C. The mixture was stirred at 0° C. for 20 minutes, and then a solution of methyl 3-(chloromethyl)benzoate (1.02 g) in tetrahydrofuran (10 ml) was added. The mixture was stirred at 25° C. for 3 hours, and then potassium tert-butoxide (1.02 g) was added. The mixture was stirred at 25° C. for 1 hour, and then evaporated. The residue was partitioned between ethyl acetate and 0.1N hydrochloric acid. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (40:1) to give tert-butyl 3-(phenothiazin-10-ylmethyl)benzoate (598 mg) as crystals.

後処理

  1. stirringThe mixture was stirred at 25° C. for 3 hours
  2. stirringThe mixture was stirred at 25° C. for 1 hour
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and 0.1N hydrochloric acid
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (40:1)

出典と根拠

ORDレコード
ord-5de86612323143d4aaac4815ed542123
出典データセット
uspto-grants-1993_05
特許番号
US05212320

反応ノート

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