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

HRID 249165노트

반응식

HRID 249165 반응식
[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

참가 물질

5

반응물 3

HCID 7108PhenothiazineHCID 3248988Methyl 3-(chloromethyl)benzoateHCID 23665647Potassium tert-butoxide2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5de86612323143d4aaac4815ed542123
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212320

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