Methanol → Hydrochloric Acid

HRID 2248607Notes

Reaction equation

HRID 2248607 reaction equation
C([Cl:4])(=O)C.CO.[C:7](=[NH:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N[N:22]1[CH:26]=[N:25][CH:24]=[N:23]1>ClCCCl.C(Cl)Cl>[ClH:4].[C:8]1([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:20][N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 136809Benzophenone imineHCID 117080471H-1,2,4-triazol-1-amine

Product 2

HCID 313Hydrochloric AcidHCID 19994944HCID 19994944, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Anhydrous methanolic HCl was prepared by dissolving 6.4 mL (90.0 mmol) of acetyl chloride in 100 mL of methanol 10.0 gm (89.3 mmol) of 1-amino-1,2,4-triazole (approximately 75% pure) was added and the solvent was removed to afford a white solid which was dried in vacuo. A portion (4.62 g, 28.7 mmol) of the solid was suspended in 100 mL of 1,2-dichloroethane and 4.0 mL (24.5 mmol) of benzophenone imine were added. The mixture was heated at reflux for 16 h. After cooling to room temperature, it was diluted with methylene chloride, washed with saturated aqueous Na2CO3, water and brine and dried (MgSO4). Removal of solvent gave an oil from which desired product was crystallized in hexanes as off-white needles; yield 3.0 (49%), mp 126°-129° C.

Workup

  1. additionwas added
  2. customthe solvent was removed
  3. customto afford a white solid which
  4. customwas dried in vacuo
  5. temperatureThe mixture was heated
  6. temperatureat reflux for 16 h
  7. washwashed with saturated aqueous Na2CO3, water and brine
  8. dry with materialdried (MgSO4)
  9. customRemoval of solvent

Sources & evidence

ORD record
ord-8bcae4ce79a949a1bda1029acf8ee58e
Source dataset
uspto-grants-1991_08
Patent number
US05041458

Reaction notes

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