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Hydrochloric Acid → 2-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid

HRID 1638923
Notes
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Reaction equation

HRID 1638923 reaction equation
ClC1[C:10]2OC(C)C[C:6]=2[C:5]([N:12]2[C:17](=[O:18])[NH:16][C:15](=[O:19])C(C#N)=[N:13]2)=[CH:4][CH:3]=1.O1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[ClH:28].[C:29]([O:32]CC)(=[O:31])[CH3:30]>>[Cl:28][C:27]1[C:26]2[O:25][CH:24]([CH3:23])[CH2:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[NH:16][C:15](=[O:19])[C:30]([C:29]([OH:32])=[O:31])=[N:13]2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 542357422-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile

Product 1

HCID 541828772-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid

Procedure

A mixture of 9.0 g of 32C, 150 mL of p-dioxane and 100 mL of 6N hydrochloric acid was stirred at reflux temperature overnight. Then 20 mL of 12N hydrochloric acid was added and the mixture was stirred at reflux temperature for 2 hours, and stripped of solvent. The residue was dissolved in ethyl acetate, the solution was washed with water, then brine, dried (MgSO4) and stripped of solvent. The residue was recrystallized from ethyl acetate/petroleum ether to give 2-(7-chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid (32D), as an amber solid, m.p.: 235°-236° C. (with decomposition).

Workup

  1. temperatureat reflux temperature overnight
  2. stirringthe mixture was stirred
  3. temperatureat reflux temperature for 2 hours
  4. washthe solution was washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. customThe residue was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-3f532028e45643f39c00a3fe2b32bff4
Source dataset
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04881967

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes