Water → HCID 86735457, compound

HRID 616248Notes

Reaction equation

HRID 616248 reaction equation
[F:1][S:2]([OH:5])(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:18]=[CH:17][C:16](=[N:19][NH2:20])[CH:15]=[CH:14]2)=[CH:9][CH:8]=1.O.[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1>C(O)C>[F:1][S:2]([OH:5])(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH:14]=[CH:15][C:16](=[N:19][N:20]=[CH:27][C:26]3[CH:29]=[CH:30][C:23]([Cl:22])=[CH:24][CH:25]=3)[CH:17]=[CH:18]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 12370274HCID 12370274, compound

Product 1

HCID 86735457HCID 86735457, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2.4 g. (7.5 mmole) of 1-(4-chlorophenyl)-4(1H)-pyridinone hydrazone fluorosulfonate, prepared by the process set forth in Example 2, in 35 ml. ethanol and 30 ml. water was added a solution of 1.27 g. (9 mmole) of p-chlorobenzaldehyde in 5 ml. ethanol. After heating the reaction mixture on the steam bath for 3 minutes, the mixture was concentrated to remove most of the ethanol, cooled and the product collected by filtration. Yield 3.1 g. (94%), recrystallized from EtOH-H2O, m.p. 252°-253° C. The elemental analyses for C, H, N and Cl were within ±0.4% of the theoretical values.

Workup

  1. temperatureAfter heating the reaction mixture on the steam bath for 3 minutes
  2. concentrationthe mixture was concentrated
  3. customto remove most of the ethanol
  4. temperaturecooled
  5. filtrationthe product collected by filtration
  6. custom(94%), recrystallized from EtOH-H2O, m.p. 252°-253° C

Sources & evidence

ORD record
ord-50ed25dc8dd042c6b1acdb77740a8cb4
Source dataset
uspto-grants-1978_02
Patent number
US04073791

Reaction notes

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