Acetic Anhydride → HCID 18989524, compound

HRID 2395627Notes

Reaction equation

HRID 2395627 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:12][NH:11][C:10](=[S:13])[N:9]1[CH2:14][CH3:15].[C:16](OC(=O)C)(=[O:18])[CH3:17]>O1CCCC1.O.C(OCC)(=O)C>[C:16]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:12][NH:11][C:10](=[S:13])[N:9]1[CH2:14][CH3:15])(=[O:18])[CH3:17]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 18989527HCID 18989527, compound

Product 1

HCID 18989524HCID 18989524, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.25 g of 5-(2-aminophenyl)-2,4-dihydro-4-ethyl-1H-[1,2,4]triazol-3-thione and 0.13 mL of acetic anhydride in 1.5 mL of tetrahydrofuran and 0.7 mL of water was stirred at 24° C. for 4 hours. The solution was diluted with 25 mL of ethyl acetate, washed with brine, and dried over MgSO4. The mixture was filtered and the filtrate was concentrated to dryness and then dissolved in 20 mL of 1N sodium hydroxide. The aqueous mixture was extracted twice with 20 mL portions of ethyl acetate. The extracts were combined, washed with brine, dried, and concentrated to dryness to give a solid. The solid was triturated with ethyl acetate:hexane (1:1 v/v) to give 140 mg of 5-(2-acetamidophenyl)-2,4-dihydro-4-ethyl-1H-[1,2,4]triazol-3-thione, mp 193°-194° C.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutiondissolved in 20 mL of 1N sodium hydroxide
  6. extractionThe aqueous mixture was extracted twice with 20 mL portions of ethyl acetate
  7. washwashed with brine
  8. customdried
  9. concentrationconcentrated to dryness
  10. customto give a solid
  11. customThe solid was triturated with ethyl acetate:hexane (1:1 v/v)

Sources & evidence

ORD record
ord-e8fc2c0328dc403dbbd6b158ab7478e8
Source dataset
uspto-grants-1996_02
Patent number
US05489598

Reaction notes

Loading…