1,1,1-Trimethoxy-2-methylpropane → 4,5-dihydro-3-methyl-2-(1-methylethyl)-4-(2-thienyl)-3H-1,3-benzodiazepine

HRID 486659

반응식

HRID 486659 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[NH:10][CH3:11].[C:17](OC)(OC)(OC)[CH:18]([CH3:20])[CH3:19]>C(O)(=O)C>[CH3:11][N:10]1[CH:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:17]1[CH:18]([CH3:20])[CH3:19]

참가 물질

4

반응물 2

HCID 404951,1,1-Trimethoxy-2-methylpropaneHCID 102633632-amino-N-methyl-alpha-(2-thienyl)benzeneethanamine

생성물 1

HCID 224144244,5-dihydro-3-methyl-2-(1-methylethyl)-4-(2-thienyl)-3H-1,3-benzodiazepine수율 25.6%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A stirred solution of 3.45 g of 2-amino-N-methyl-α-(2-thienyl)benzeneethaneamine and 13.34 g of trimethyl orthoisobutyrate was treated rapidly with 3.8 ml of glacial acetic acid. The reaction mixture was refluxed for 8 hours and cooled to room temperature overnight. The mixture was concentrated on a rotary evaporator at 70° C. After standing overnight under refrigeration, the residue was dissolved in 60 ml of 10% hydrochloric acid solution and extracted with diethyl ether (2×50 ml). The aqueous phase was basified with 10% sodium hydroxide solution and extracted with dichloromethane (2×75 ml). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to an oil. The oil was purified by HPLC (Water's Associates Prep LC/System 500; silica gel; sample applied in dichloromethane; methanol as eluent). Concentration of the appropriate fractions yielded 1.08 g of 4,5-dihydro-3-methyl-2-(1-methylethyl)-4-(2-thienyl)-3H-1,3-benzodiazepine as an oil.

후처리

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. concentrationThe mixture was concentrated on a rotary evaporator at 70° C
  3. dissolutionthe residue was dissolved in 60 ml of 10% hydrochloric acid solution
  4. extractionextracted with diethyl ether (2×50 ml)
  5. extractionextracted with dichloromethane (2×75 ml)
  6. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThe oil was purified by HPLC (Water's Associates Prep LC/System 500; silica gel; sample applied in dichloromethane; methanol as eluent)

출처 및 근거

ORD 기록
ord-6689ab3b2f4e4e9a964f2028f5c749cf
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292760

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