1,1'-Thiocarbonyldiimidazole → HCID 14099454, compound

HRID 569777Notes

Reaction equation

HRID 569777 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.C1N=CN([C:20](N2C=NC=C2)=[S:21])C=1>CN(C=O)C>[N:1]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[C:20]=[S:21]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 14099454HCID 14099454, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10.0 g of 6-(4-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone in 200 ml of DMF is added dropwise over a period of three hours to a stirred solution of 10.5 g of 1,1-thiocarbonyldiimidazole while cooling in an ice-water bath. After completion of the addition, stirring is continued for 30 minutes at icebath temperature followed by an additional 30 minutes at room temperature. The reaction mixture is filtered and the filtrate is diluted with 500 ml of water. The aqueous suspension is cooled in ice and the solid is filtered, washed with water, and dried to yield 10.8 g of the product, 4,5-dihydro-6-[4-(isothiocyano)phenyl]3(2H)pyridazinone as off-white powder, mp 181.5°-183° C.

Workup

  1. temperaturewhile cooling in an ice-water bath
  2. additionAfter completion of the addition
  3. waitfollowed by an additional 30 minutes at room temperature
  4. filtrationThe reaction mixture is filtered
  5. additionthe filtrate is diluted with 500 ml of water
  6. temperatureThe aqueous suspension is cooled in ice
  7. filtrationthe solid is filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-0601508287544010a67ba05fc8038210
Source dataset
uspto-grants-1988_03
Patent number
US04734415

Reaction notes

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