Trimethyl orthobeznoate → HCID 22414484、化合物

HRID 486663

反応式

HRID 486663 の反応式
[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][C:16]=1[CH3:17])[NH:10][CH3:11].CO[C:20](OC)(OC)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(=O)C>[CH3:11][N:10]1[CH:9]([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[CH3:17])[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:20]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

4

反応物 2

HCID 69720Trimethyl orthobeznoateHCID 130176Compound 7189

生成物 1

HCID 22414484HCID 22414484、化合物収率 91.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A stirred solution of 2.19 g of 2-amino-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine and 9.88 g of trimethyl orthobenzoate was treated rapidly with 2.4 ml of glacial acetic acid, and heated under reflux for 8 hours. The solution was concentrated at 75° C. on a rotary evaporator (vacuum pump) to a syrup. The syrup was then partioned between 10% hydrochloric acid solution (50 ml) and ether. The aqueous phase was extracted again with ether, basified with 10% sodium hydroxide solution (60 ml) and extracted with dichloromethane (2×100 ml). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to an oil. The oil was purified by preparative HPLC (Water's Associates Prep LC/System 500A, silica gel, sample applied in dichloromethane, 2% triethylamine in methanol as the eluent). Concentration of the appropriate fractions yielded 2.70 g of 4,5-dihydro-3-methyl-4-(3-methyl-2-thienyl)-2-phenyl-3H-1,3-benzodiazepine as an oil.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 8 hours
  3. concentrationThe solution was concentrated at 75° C. on a rotary evaporator (vacuum pump) to a syrup
  4. extractionThe aqueous phase was extracted again with ether
  5. extractionextracted with dichloromethane (2×100 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 preparative HPLC (Water'

出典と根拠

ORDレコード
ord-b2402df29d2f4739ade6369bee54556e
出典データセット
uspto-grants-1994_03
特許番号
US05292760

関連ノート

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