Tetrahydrofuran → 4'Chloro-2-[bis(p-dimethylaminophenyl)methoxy]acetanilide

HRID 1995245노트

반응식

HRID 1995245 반응식
[CH3:1][N:2]([C:4]1[CH:20]=[CH:19][C:7]([CH:8]([OH:18])[C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[CH3:3].COC.[Cl:24][C:25]1[CH:35]=[CH:34][C:28]([NH:29][C:30](=[O:33])[CH2:31]O)=[CH:27][CH:26]=1.O1CCCC1>C(O)(=O)C.CCCCCC>[Cl:24][C:25]1[CH:35]=[CH:34][C:28]([NH:29][C:30](=[O:33])[CH2:31][O:18][CH:8]([C:7]2[CH:19]=[CH:20][C:4]([N:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=2)[C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:16])[CH3:17])=[CH:11][CH:10]=2)=[CH:27][CH:26]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8254Dimethyl EtherHCID 927424,4'-Bis(dimethylamino)benzhydrolHCID 13600665N-(4-chlorophenyl)-2-hydroxyacetamide

생성물 1

HCID 204880394'Chloro-2-[bis(p-dimethylaminophenyl)methoxy]acetanilide

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8058Hexane용매

실험 절차

A solution of 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether, (8.0 g, 0.028 mole), p-chloroglycolanilide (5.23 g, 0.028 mole), 170 ml of tetrahydro-furan, 120 ml of n-hexane, and 4.5 ml of glacial acetic acid was refluxed for about 8.5 hours, replacing solvent as distillate was removed. Color was then discharged by the addition of 20 drops of tetramethylguanidine and the solution was filtered hot. Hexane was added to the filtrate, yielding a light green oil. The oil was removed and the hexane solution, on cooling, gave a light blue solid. The solid was filtered, washed with petroleum ether and dried. Recrystallization from 150 ml methylcyclohexane/40 ml acetone gave a yellow-white, gummy solid. This was recrystallized from VM&P naphtha to give a fine white powder, mp 137.5°-140° C.

후처리

  1. customwas removed
  2. additionColor was then discharged by the addition of 20 drops of tetramethylguanidine
  3. filtrationthe solution was filtered hot
  4. additionHexane was added to the filtrate
  5. customyielding a light green oil
  6. customThe oil was removed
  7. temperaturethe hexane solution, on cooling
  8. customgave a light blue solid
  9. filtrationThe solid was filtered
  10. washwashed with petroleum ether
  11. customdried
  12. customRecrystallization from 150 ml methylcyclohexane/40 ml acetone
  13. customgave a yellow-white, gummy solid
  14. customThis was recrystallized from VM&P naphtha
  15. customto give a fine white powder, mp 137.5°-140° C.

출처 및 근거

ORD 기록
ord-4313900868d54d3180b5b0f2c9cab034
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04403792

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