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

HRID 66932

Reaction equation

HRID 66932 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-8adc481142ff434b8be94e97fb67ded2
Source dataset
uspto-grants-1982_08
Patent number
US04343939

Linked notes

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