N-Methylformanilide → HCID 23354006, compound

HRID 235263Notes

Reaction equation

HRID 235263 reaction equation
CN([CH:9]=[O:10])C1C=CC=CC=1.[CH3:11][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>[CH:9]([C:31]1[S:32][C:28]2[CH2:27][CH2:26][CH2:25][C:21]3[C:20](=[N:19][N:18]([C:15]4[CH:14]=[CH:13][C:12]([CH3:11])=[CH:17][CH:16]=4)[C:23](=[O:24])[CH:22]=3)[C:29]=2[CH:30]=1)=[O:10]

Participants

4

Reactant 2

HCID 66737N-MethylformanilideHCID 10495037HCID 10495037, compound

Product 1

HCID 23354006HCID 23354006, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 24646Chlorine monoxideSolvent

Procedure

A mixture of 4.7 g of N-methylformanilide in 3.3 ml of phosphrus oxychloride was stirred at room temperature for an hour and 5.4 g of 2-(4-methylphenyl)-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 chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel column using a mixed solvent of hexane and ethyl acetate (2:1) as an eluent. The solid was recrystallized from a mixed solvent of ethanol and ethyl acetate to give 3.5 g of 9-formyl-2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one as a pale brown powder, melting at 127°-129° C.

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. additionthe mixture was poured into ice-cold water
  3. extractionextracted with chloroform
  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 column
  8. customThe solid was recrystallized from a mixed solvent of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-2e0272fa8db241a0a24d3b733a26245d
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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