HCID 414534, compound → HCID 178450192, compound

HRID 268269Notes

Reaction equation

HRID 268269 reaction equation
N[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[ClH:13].[NH:14]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]3[N:33]=[CH:32][NH:31][C:29]3=2)[N:24]=[C:23]([CH3:34])[CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[OH2:6].[ClH:13].[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:14][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]4[N:33]=[CH:32][NH:31][C:29]4=3)[N:24]=[C:23]([CH3:34])[CH:22]=2)=[CH:9][CH:8]=1)(=[O:6])[CH2:4][CH2:3][CH3:2].[C:5]([C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]4[N:33]=[CH:32][NH:31][C:29]4=3)[N:24]=[C:23]([CH3:34])[CH:22]=2)=[CH:16][CH:17]=1)(=[O:6])[CH2:4][CH2:3][CH3:2].[ClH:13]

Participants

4

Reactant 2

HCID 414534HCID 414534, compoundHCID 178428198HCID 178428198, compound

Product 1

HCID 178450192HCID 178450192, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 16.3 g. (0.1 m) of 4-aminobutyrophenone, 21.7 g. (0.1 m) of the compound of Example I, C. and 500 ml. of ethanol was refluxed overnight. The solution was concentrated in vacuo to dryness. The soft, yellow solid was dissolved in 300 ml. of MeOH and filtered. The MeOH filtrate was evaporated to a volume of 50 ml. then chilled. The product was filtered, washed with ether and oven-dried (110°C) to give 24 g. m.p. 209°-230°C. A second recrystallization from MeOH yielded 22 g., m.p. 205°-235°C.

Workup

  1. additionA mixture of 16.3 g
  2. concentrationThe solution was concentrated in vacuo to dryness
  3. dissolutionThe soft, yellow solid was dissolved in 300 ml
  4. filtrationof MeOH and filtered
  5. customThe MeOH filtrate was evaporated to a volume of 50 ml
  6. temperaturethen chilled
  7. filtrationThe product was filtered
  8. washwashed with ether
  9. customoven-dried (110°C)
  10. customto give 24 g
  11. customA second recrystallization from MeOH
  12. customyielded 22 g

Sources & evidence

ORD record
ord-df91841f024e439fba321f4dc825b2aa
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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