Hydrochloric Acid → HCID 178437927, compound

HRID 1416418Notes

Reaction equation

HRID 1416418 reaction equation
[CH2:1]([C:3]1[S:7][C:6](=[NH:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:26][N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[N:4]=1)[CH3:2].[C:27]12[C:35](=[O:36])[O:34][C:32](=[O:33])[C:28]=1[CH2:29][CH2:30][CH2:31]2.O.Cl>CN(C)C=O.C(O)C>[CH2:1]([C:3]1[S:7][C:6](=[N:8][C:35]([C:27]2[CH2:31][CH2:30][CH2:29][C:28]=2[C:32]([OH:34])=[O:33])=[O:36])[N:5]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][N:24]=[N:25][N:26]=3)=[CH:14][CH:15]=2)[N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3248541H,3H,4H,5H,6H-cyclopenta(c)furan-1,3-dioneHCID 178437930HCID 178437930, compound

Product 1

HCID 178437927HCID 178437927, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

In 30 ml of N,N-dimethylformamide, 3.63 g of 5-ethyl-2-imino-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1,3,4-thiadiazoline was dissolved, followed by the addition of 1.44 g of 1-cyclopentene-1,2-dicarboxylic anhydride. The resulting mixture was stirred at room temperature for 6 hours. To the reaction mixture, 200 ml of water and 5 ml of hydrochloric acid were added. The powders so precipitated were collected by filtration. The powders so obtained were suspended in 100 ml of ethanol and the resulting suspension was heated under reflux for 20 minutes. The powders were collected by filtration, washed successively with ethanol and diethyl ether and then dried, whereby 4.53 g of the title compound was obtained.

Workup

  1. customThe powders so precipitated
  2. filtrationwere collected by filtration
  3. customThe powders so obtained
  4. temperaturethe resulting suspension was heated
  5. temperatureunder reflux for 20 minutes
  6. filtrationThe powders were collected by filtration
  7. washwashed successively with ethanol and diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-d1e98fe9b89244cf8b0c977f74c3c601
Source dataset
uspto-grants-1999_06
Patent number
US05912353

Reaction notes

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