N-Methylformanilide → HCID 23353992, compound

HRID 235269Notes

Reaction equation

HRID 235269 reaction equation
CN([CH:9]=[O:10])C1C=CC=CC=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]3[CH2:25][CH2:26][CH2:27][C:28]4[S:32][CH:31]=[CH:30][C:29]=4[C:20]3=[N:19]2)=[CH:14][CH:13]=1>O(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]3[CH2:25][CH2:26][CH2:27][C:28]4[S:32][C:31]([CH:9]=[O:10])=[CH:30][C:29]=4[C:20]3=[N:19]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 66737N-MethylformanilideHCID 10782547HCID 10782547, compound

Product 1

HCID 23353992HCID 23353992, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 24646Chlorine monoxideSolvent

Procedure

A mixture of 0.45 g of N-methylformanilide in 0.33 ml of phosphrus oxychloride was stirred at room temperature for an hour and 0.5 g of 2-(4 -chlorophenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one was added thereto. After stirring at room temperature for 2 hours, the mixture was poured into ice-cold water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel (SiO2 :40 g) column using chloroform as an eluent. The resulting solid was recrystallized from a mixed solvent of chloroform and ethanol to give 0.25 g of 2-(4-chlorophenyl)-9-formyl-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]-cyclohepta[1,2-c]pyridazin-3-one as a pale yellow powder, melting at 170°-172° C.

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. additionthe mixture was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on a silica gel (SiO2 :40 g) column
  8. customThe resulting solid was recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-ffef500251f94e9dae2e141c05282046
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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