Ammonia → HCID 12666068, compound

HRID 848583Notes

Reaction equation

HRID 848583 reaction equation
CO[C:3](=[O:19])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:15]([CH3:16])=[N:14][N:13]=[C:12]1[CH2:17]Cl.[NH3:20].[I-].[K+]>O1CCCC1.CO>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]2[N:11]3[C:15]([CH3:16])=[N:14][N:13]=[C:12]3[CH2:17][NH:20][C:3](=[O:19])[C:4]=2[CH:9]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 4875Potassium IodideHCID 12666067HCID 12666067, compound

Product 1

HCID 12666068HCID 12666068, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 5-chloro-2-[3-(chloromethyl)-5-methyl-4H-1,2,4-triazol-4-yl]benzoic acid methyl ester (VIb)(300 mg., 1 mmole) in tetrahydrofuran (THF) (10 ml.) was cooled, under nitrogen, in an ice bath and treated with 8 ml. of a saturated solution of ammonia in methanol. The mixture was kept in the ice bath for 20 minutes and at ambient temperature for one hour. At this time there was no reaction by thin layer chromatography (TLC). The mixture was therefore treated with potassium iodide (166 mg., 1 mmole) and kept at ambient temperature for 18 hours. It was concentrated in vacuo, and the residue was mixed with water and extracted with chloroform. The extract was washed with brine, dried (Na2SO4) and concentrated. The residue was crystallized from a methanol/ethyl acetate mixture to give 0.169 g., melting point 253.5°-255.5° and 0.026 g., melting point 251°-252.5°. The mixture melting point with that of an authentic sample of the titled compound (VIIa) was 261.5°-264.5°. The first crop was recrystallized from a methanol/ethyl acetate mixture, seeding with an authentic sample, to give 0.110 g., melting point 262°-264°. This was identical to the authentic sample of (VIIa) by ir comparison.

Workup

  1. additiontreated with 8 ml
  2. customno reaction by thin layer chromatography (TLC)
  3. concentrationIt was concentrated in vacuo
  4. additionthe residue was mixed with water
  5. extractionextracted with chloroform
  6. washThe extract was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was crystallized from a methanol/ethyl acetate mixture
  10. customto give 0.169 g

Sources & evidence

ORD record
ord-ace8c8a523fc4c3ea1668117b202f462
Source dataset
uspto-grants-1981_10
Patent number
US04296239

Reaction notes

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