Dichloromaleic anhydride → HCID 86740704, compound

HRID 1380083Notes

Reaction equation

HRID 1380083 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:22])[N:7]3[CH2:14][CH2:13][C:12](=[CH:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:8]3=[N:9][C:10]=2[CH:11]=1.[Cl:23][C:24]1[C:25]([O:27][C:28](=[O:31])[C:29]=1[Cl:30])=[O:26]>O1CCCC1>[CH:15](=[C:12]1[C:8]2=[N:9][C:10]3[CH:11]=[C:2]([NH:1][C:28](/[C:29](/[Cl:30])=[C:24](/[Cl:23])\[C:25]([OH:27])=[O:26])=[O:31])[CH:3]=[CH:4][C:5]=3[C:6](=[O:22])[N:7]2[CH2:14][CH2:13]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 70728Dichloromaleic anhydrideHCID 54343992HCID 54343992, compound

Product 1

HCID 86740704HCID 86740704, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-amino-3-benzylidene-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline-9-one (2 g) was reacted with 2,3-dichloro-maleic anhydride (3.46 g) in tetrahydrofuran (130 ml) under stirring at the reflux temperature for 3 hours. After cooling the solution was evaporated in vacuo to dryness: the residue was suspended in hot ethyl acetate and filtered. Crystallization from CH2Cl2 -ethyl acetate gave 1 g of (Z)-3-[N-(3-benzylidene-9-oxo-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-6-yl)-aminocarbonyl]-2,3-dichloro-2-propenoic acid, m.p. 160°-165° C. (dec.),

Workup

  1. temperatureAfter cooling the solution
  2. customwas evaporated in vacuo to dryness
  3. filtrationfiltered
  4. customCrystallization from CH2Cl2 -ethyl acetate

Sources & evidence

ORD record
ord-172b758317174b9f9afc6d5124f52d62
Source dataset
uspto-grants-1986_04
Patent number
US04579847

Reaction notes

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