Triethylamine → HCID 178427938, compound

HRID 260348Notes

Reaction equation

HRID 260348 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[OH:10].C(N(CC)CC)C.Cl[S:19]([C:22]1[N:26]=[CH:25][NH:24][N:23]=1)(=[O:21])=[O:20]>O1CCCC1>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[O:10][S:19]([C:22]1[N:26]=[CH:25][NH:24][N:23]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 873052,4-Dichloro-m-cresolHCID 178527437HCID 178527437, compound

Product 1

HCID 178427938HCID 178427938, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.33 g of 2.4-dichloro-3-methylphenol was dissolved in 15 ml of tetrahydrofuran, and 1.84 ml of triethylamine was added while stirring the solution. Then, 2.0 g of 3-chlorosulfonyl-1,2,4-triazole was gradually added while cooling with ice and stirring the solution. Then, the solution was stirred at room temperature for 14 hours. Tetrahydrofuran was removed by distillation at reduced pressure, 2N hydrochloric acid was added, and extracted with ethyl acetate. The organic layer was washed with brine, and dried with magnesium sulfate. Then, the solvent was removed by distillation, so that coarse crystals were obtained. The coarse crystals were recrystallized from n-hexane/ethyl acetate, so that 2.25 g of the titled compound was obtained.

Workup

  1. temperaturewhile cooling with ice
  2. stirringstirring the solution
  3. stirringThen, the solution was stirred at room temperature for 14 hours
  4. customTetrahydrofuran was removed by distillation at reduced pressure, 2N hydrochloric acid
  5. additionwas added
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried with magnesium sulfate
  9. customThen, the solvent was removed by distillation
  10. customso that coarse crystals were obtained
  11. customThe coarse crystals were recrystallized from n-hexane/ethyl acetate, so that 2.25 g of the titled compound
  12. customwas obtained

Sources & evidence

ORD record
ord-edafaff699a74bd9bec67719cfb6ebbc
Source dataset
uspto-grants-1996_06
Patent number
US05527818

Reaction notes

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