Bis(2-chloroethyl) ether → 5-Morpholinobenzo[b]thiophene

HRID 979565

반응식

HRID 979565 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.Cl[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Cl.[OH-].[Na+]>>[O:14]1[CH2:15][CH2:16][N:1]([C:2]2[CH:10]=[CH:9][C:5]3[S:6][CH:7]=[CH:8][C:4]=3[CH:3]=2)[CH2:12][CH2:13]1

참가 물질

4

반응물 3

HCID 8115Bis(2-chloroethyl) etherHCID 14798Sodium HydroxideHCID 288032Benzo(b)thiophen-5-amine

생성물 1

HCID 139229065-Morpholinobenzo[b]thiophene수율 69.3%

실험 절차

5-Aminobenzo[b]thiophene (5.4 g, 0.0362 mole), bis-(2-chloroethyl)ether (5.2 g, 0.0364 mole) and 40% aqueous NaOH (0.073 mole) were stirred vigorously and heated to refluxing for 22 hours. The cooled mixture was extracted with CHCl3. Evaporation of the washed and dried CHCl3 extract under reduced pressure left 7.0 g (88%) of the crude product as a slightly oily, dark yellow solid. This material was combined with 1.75 g of comparable crude product from a previous run. Recrystallization from CH3CN afforded 5.50 g of 5-morpholinobenzo[b]thiophene, m.p. 127°-132° C., that was characterized by nmr.

후처리

  1. temperatureheated
  2. temperatureto refluxing for 22 hours
  3. extractionThe cooled mixture was extracted with CHCl3
  4. customEvaporation of the
  5. washwashed
  6. extractiondried CHCl3 extract under reduced pressure
  7. waitleft 7.0 g (88%) of the crude product as a slightly oily, dark yellow solid
  8. customRecrystallization from CH3CN

출처 및 근거

ORD 기록
ord-c26d72fc650d46f6ba647da085ccbccc
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04668697

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