Triethylamine → HCID 136139978, compound

HRID 344602Notes

Reaction equation

HRID 344602 reaction equation
C([N:3]([CH2:6]C)CC)C.[Cl:8][C:9]1[C:17]2[O:16][CH:15]([CH3:18])[CH2:14][C:13]=2[C:12]([NH:19][N:20]=[C:21]([CH3:25])C(O)=O)=[CH:11][CH:10]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:8][C:9]1[C:17]2[O:16][CH:15]([CH3:18])[CH2:14][C:13]=2[C:12]([N:19]2[C:6](=[O:33])[NH:3][C:21]([CH3:25])=[N:20]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86743514HCID 86743514, compound

Product 1

HCID 136139978HCID 136139978, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.1 g of triethylamine was added to a stirred mixture of 5.0 g of 33A and 100 mL of toluene, then 1.9 g of diphenylphosphoryl azide was added and over two hours the mixture was heated to and held at reflux temperature. The resulting mixture was poured into 110 mL of 10% w:v aqueous ice-cold potassium hydroxide solution. Two liquid phases resulted and were separated. The aqueous phase was acidified with 12N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, then with brine, dried (MgSO4) and stipped of solvent. The residue was recrystallized from ethyl acetate/hexane to give 2-(7-chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-5-methyl-2H-1,2,4-triazol-3(4H)-one (33B), as a colorless solid, m.p.: 208°-209° C.

Workup

  1. temperaturewas heated to and
  2. temperatureat reflux temperature
  3. additionThe resulting mixture was poured into 110 mL of 10%
  4. customTwo liquid phases resulted
  5. customwere separated
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialwith brine, dried (MgSO4)
  9. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a40eb80a87e945d09be356373c9da1f1
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Reaction notes

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