Dimethylformamide → HCID 14986975, compound

HRID 727787Notes

Reaction equation

HRID 727787 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:18](=[O:19])[CH2:17][CH:16]3[CH2:20][S:21][C:22]4[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:23]=4[C:15]3=[N:14]2)=[CH:9][CH:8]=1.[H-].[Na+].[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35]Cl>O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:18](=[O:19])[CH2:17][CH:16]3[CH2:20][S:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:35][CH2:34][CH2:33][N:32]([CH3:37])[CH3:31])=[CH:24][C:23]=4[C:15]3=[N:14]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 14098706HCID 14098706, compound

Product 1

HCID 14986975HCID 14986975, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of dry dimethylformamide is added 4.5 g of 2-(4-chlorophenyl)-9-hydroxy-2,3,4,4a-tetrahydro-5H-(1)benzothiopyrano[4,3-c]pyridazin-3-one, and 0.7 g of 60% sodium hydride is added thereto while stirring at room temperature. After stirring at room temperature for 1 hour and addition of 2 g of 3-dimethylaminopropyl chloride, the mixture is stirred under heating at 40°-50° C. for 3 hours. After the completion of the reaction, the reaction mixture is poured into a large amount of water and the mixture is extracted with chloroform. The extract is washed with water and dried over anhydrous magnesium sulfate. Thereafter, the solvent is distilled off. The residue is subjected to column chromatography and the eluate is converted into its fumarate to give 0.52 g of 2-(4-chlorophenyl)-9-(3-dimethylaminopropoxy)-2,3,4,4a-tetrahydro-5H-(1)benzothiopyrano[4,3-c]pyridazin-3-one.fumarate, as yellow crystals, m.p. 208°-210° C.

Workup

  1. additionis added
  2. stirringAfter stirring at room temperature for 1 hour
  3. stirringthe mixture is stirred
  4. temperatureunder heating at 40°-50° C. for 3 hours
  5. customAfter the completion of the reaction
  6. extractionthe mixture is extracted with chloroform
  7. washThe extract is washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThereafter, the solvent is distilled off

Sources & evidence

ORD record
ord-ac673358575748f2a03ec62139db7cff
Source dataset
uspto-grants-1991_09
Patent number
US05045541

Reaction notes

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