Propanedioyl dichloride → HCID 178425409, compound

HRID 1084971Notes

Reaction equation

HRID 1084971 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][S:11]([C:14]1[N:18]=[C:17]([NH2:19])[NH:16][N:15]=1)(=[O:13])=[O:12].[C:20](Cl)(=[O:25])[CH2:21][C:22](Cl)=[O:23]>C(#N)C>[OH:23][C:22]1[CH:21]=[C:20]([OH:25])[N:16]2[N:15]=[C:14]([S:11]([NH:10][C:3]3[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=3[Cl:1])(=[O:13])=[O:12])[N:18]=[C:17]2[N:19]=1

Participants

4

Reactant 2

HCID 74269Propanedioyl dichlorideHCID 178425411HCID 178425411, compound

Product 1

HCID 178425409HCID 178425409, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2.52 grams (g) (0.0078 moles) of N-(3-(((2,6-dichloro-3-methylphenyl)amino)sulfonyl)-1H-1,2,4-triazol-5-yl)amine in 100 milliliters (mL) of dry acetonitrile under nitrogen was added 1.5 g (0.01 moles) of freshly distilled malonyl chloride. The mixture was stirred at ambient temperature overnight (14 hr) and a yellow precipitate formed. The solid product was collected by filtration and dried; mp 280°-282° C. (decomposes). The filtrate was found to contain additional product which was recovered by concentrating the filtrate to dryness. The combined yield of product was 2.58 g (85 percent yield).

Workup

  1. customa yellow precipitate formed
  2. filtrationThe solid product was collected by filtration
  3. customdried
  4. customwas recovered
  5. concentrationby concentrating the filtrate to dryness

Sources & evidence

ORD record
ord-21ad75bdb0b04a7398623c4173229beb
Source dataset
uspto-grants-1991_04
Patent number
US05006656

Reaction notes

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