Triethylamine → HCID 178516717, compound

HRID 2227450Notes

Reaction equation

HRID 2227450 reaction equation
C(O[C:4]1[C:5](=[O:20])[C:6](=[O:19])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)C.Cl.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([C:30]2[NH:34][N:33]=[N:32][N:31]=2)[CH:24]=1.C(N(CC)CC)C>C(#N)C>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:4]2[C:5](=[O:20])[C:6](=[O:19])[C:7]=2[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=2)=[C:25]([C:30]2[NH:34][N:33]=[N:32][N:31]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18473839HCID 18473839, compoundHCID 178479027HCID 178479027, compound

Product 1

HCID 178516717HCID 178516717, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.29 g of 3-ethoxy-4-(3-trifluoromethylphenylamino)-3-cyclobuten-1,2-dione in 25 mL of acetonitrile was added 0.28 g of 4-bromo-2-(1H-tetrazol-5-yl)-phenylamine hydrochloride and 0.1 g of triethylamine. The reaction mixture was heated at reflux for 62 hours, the reaction mixture was concentrated to an oil, the oil was dissolved in ethyl alcohol (96%), to this solution was added hydrochloric acid (4M) and a solid precipitated. The product was isolated by filtration, washed with water and dried by pulling air though it on a glass filter. Yield 0.26 g (56%) mp. 150-165° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 62 hours
  3. concentrationthe reaction mixture was concentrated to an oil
  4. dissolutionthe oil was dissolved in ethyl alcohol (96%), to this solution
  5. additionwas added hydrochloric acid (4M)
  6. customa solid precipitated
  7. customThe product was isolated by filtration
  8. washwashed with water
  9. customdried
  10. filtrationfilter

Sources & evidence

ORD record
ord-ec8c8b6b5441499482947c92af11c813
Source dataset
uspto-grants-2002_07
Patent number
US06413996B2

Reaction notes

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