1H-benzotriazol-1-yl 2,2-diphenyl-1,3-benzodioxol-5-carboxylate → HCID 178429713, compound

HRID 1755926Notes

Reaction equation

HRID 1755926 reaction equation
O.S.[Na].[N:4]([CH2:7][C:8]1[N:18]=[C:11]2[N:12]=[C:13]([CH3:17])[CH:14]=[C:15]([SH:16])[N:10]2[N:9]=1)=[N+]=[N-].[C:19]1([C:25]2([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[O:29][C:28]3[CH:30]=[CH:31][C:32]([C:34](ON4C5C=CC=CC=5N=N4)=[O:35])=[CH:33][C:27]=3[O:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[SH:16][C:15]1[N:10]2[N:9]=[C:8]([CH2:7][NH:4][C:34]([C:32]3[CH:31]=[CH:30][C:28]4[O:29][C:25]([C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[O:26][C:27]=4[CH:33]=3)=[O:35])[N:18]=[C:11]2[N:12]=[C:13]([CH3:17])[CH:14]=1

Participants

5

Reactant 3

HCID 115901781H-benzotriazol-1-yl 2,2-diphenyl-1,3-benzodioxol-5-carboxylateHCID 53442613Sodium hydrogen sulfide hydrateHCID 178429715HCID 178429715, compound

Product 1

HCID 178429713HCID 178429713, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A dried solution of 2.0 g of sodium hydrogen sulphide monohydrate (drying agent molecular sieve 4 Å) in 100 ml of dimethylformamide is treated with 2.2 g of 2-azidomethyl-5-methyl[1.2.4]triazolo[1,5-a]pyrimidine-7-thiol and stirred until the evolution of gas has finished (about 15 minutes). Thereupon, 4.35 g of 1H-benzotriazol-1-yl 2,2-diphenyl-1,3-benzodioxol-5-carboxylate are added and the reaction mixture is stirred at room temperature for 20 hours and at 45° C. for 24 hours. The solvent is evaporated in a high vacuum, the residue is taken up in 200 ml of ethyl acetate and 200 ml of water and stirred in an ice bath for 30 minutes. The resulting precipitate is filtered off under suction, washed with water and ethyl acetate and dried in a vacuum at 40° C. The yellow product is dissolved in 100 ml of methanol, a small amount of insoluble material is removed by filtration and the filtrate is concentrated to dryness. The residue in 100 ml of acetonitrile is heated at reflux on a steam bath for 1 hour. After cooling in an ice bath the product is filtered off under suction and dried. There are obtained 4.25 g of N-[(7-mercapto-5-methyl-s-triazolo[1,5-a]pyrimidin-2-yl)methyl]-2,2-diphenyl-1,3-benzodioxol-5-carboxamide as a yellow solid of melting point 267°-271° C. (dec.).

Workup

  1. custom(about 15 minutes)
  2. stirringthe reaction mixture is stirred at room temperature for 20 hours and at 45° C. for 24 hours
  3. customThe solvent is evaporated in a high vacuum
  4. stirring200 ml of water and stirred in an ice bath for 30 minutes
  5. filtrationThe resulting precipitate is filtered off under suction
  6. washwashed with water and ethyl acetate
  7. customdried in a vacuum at 40° C
  8. dissolutionThe yellow product is dissolved in 100 ml of methanol
  9. customa small amount of insoluble material is removed by filtration
  10. concentrationthe filtrate is concentrated to dryness
  11. temperatureThe residue in 100 ml of acetonitrile is heated
  12. temperatureat reflux on a steam bath for 1 hour
  13. temperatureAfter cooling in an ice bath the product
  14. filtrationis filtered off under suction
  15. customdried

Sources & evidence

ORD record
ord-8028170fb0694322808186847a12ab96
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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