Dimethylformamide → HCID 13827299, compound

HRID 978664Notes

Reaction equation

HRID 978664 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18](=[O:22])[NH:17][N:16]=[CH:15]3)=[CH:6][CH:5]=1)([OH:3])=O.S(Cl)(Cl)=O.CN(C=O)C.[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36][NH-:37]>C1(C)C=CC=CC=1.C1COCC1>[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36][NH:37][C:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18](=[O:22])[NH:17][N:16]=[CH:15]3)=[CH:6][CH:5]=1)=[O:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 13827298HCID 13827298, compoundHCID 131715134HCID 131715134, compound

Product 1

HCID 13827299HCID 13827299, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
42 °C

Procedure

Trans-6-(2-(4-Carboxyphenyl)ethenyl]-1(2H)-phthalazinone (46 g), thionyl chloride (315 ml) and DMF (2 ml) were mixed and heated slowly to 42° C. and maintained at 42°-48° C. until the gas evolution subsided. The reaction mixture was diluted with toluene and filtered to give the crude acid chloride (52 g). The crude acid chloride (25 g) was dissolved in THF (1250 ml) and 3-dimethylaminopropylamide (250 ml) was added dropwise. After stirring overnight at room temperature the precipitate was filtered, washed with ether (2 l) and then dried to give the amide (13.5 g). The amide was purified via the hydrochloride salt, mp 287° C.

Workup

  1. temperaturemaintained at 42°-48° C. until the gas evolution
  2. filtrationfiltered
  3. customto give the crude acid chloride (52 g)
  4. filtrationwas filtered
  5. washwashed with ether (2 l)
  6. customdried

Sources & evidence

ORD record
ord-bc464b8af3f84ab28928e7c470a820b6
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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