Oxalic Acid → 3-{2-[4-(8-Chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone

HRID 1075880노트

반응식

HRID 1075880 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH:8]=[C:7]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][N:25]4[CH2:29][CH2:28][O:27][C:26]4=[O:30])[CH2:19][CH2:18]3)[C:6]=2[CH:31]=1.[BH4-].[Na+].C(O)(=O)C(O)=O>COCCOCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][CH:7]([N:17]3[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][N:25]4[CH2:29][CH2:28][O:27][C:26]4=[O:30])[CH2:21][CH2:22]3)[C:6]=2[CH:31]=1

참가 물질

5

반응물 3

HCID 971Oxalic AcidHCID 4311764Sodium borohydrideHCID 214160983-[2-[4-(8-Chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone

생성물 1

HCID 214161293-{2-[4-(8-Chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone

시약·촉매·용매 1

HCID 8150Diglyme용매2회

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온도
100 °C

실험 절차

1.0 G. of 3-{2-[4-(8-chloro-2-methyl-dibenzo[b,f]thiepin10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone is stirred at room temperature with 50 ml. of diethyleneglycol dimethyl ether (diglyme) and 0.6 g. of sodium borohydride for 30 minutes under an atmosphere of argon. Thereafter, a solution of 2.8 g. of oxalic acid (C2H2O4 . 2H2O) in 15 ml. of diglyme is added dropwise at 20°-30°C. The mixture is stirred at 100°C. for 4 hours, and subsequently evaporated under reduced pressure. The residue is taken up in 2N sodium hydroxide and water, and extracted three times with 100 ml. of benzene each time. The combined benzene phases are washed with water, dried over magnesium sulfate, filtered and concentrated. The crystalline residue is recrystallized from ethyl acetate/petroleum ether (low boiling), whereby there is obtained 3-{2-[4-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone, having a melting point of 184°-186°C. The maleate crystallizes from methanol/ether and melts at 174°-175°C.

후처리

  1. customsubsequently evaporated under reduced pressure
  2. extractionwater, and extracted three times with 100 ml
  3. washThe combined benzene phases are washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crystalline residue is recrystallized from ethyl acetate/petroleum ether (low boiling)

출처 및 근거

ORD 기록
ord-95844fd00ed24275b7b8d8fd16cc936c
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03954764

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