Hydrochloric Acid → HCID 178420196, compound

HRID 2248348Notes

Reaction equation

HRID 2248348 reaction equation
[C:1]1([CH:7]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[N:14][N:13](O)[C:12]=3[CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].BrCC(OCC)=O.Cl>CS(C)=O>[C:1]1([CH:7]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[C:8]2[CH:9]=[CH:10][C:11]3[NH:15][N:14]=[N:13][C:12]=3[CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate2×HCID 14990935HCID 14990935, compound

Product 1

HCID 178420196HCID 178420196, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5.85 parts of 6-[phenyl(1H-1,2,4-triazol-1-yl)methyl]-1H-benzotriazol-1-ol, 1.4 parts of potassium carbonate and 27.5 parts of dimethyl sulfoxide was stirred for 30 minutes at 50° C. After cooling, 3.55 parts of ethyl 2-bromoacetate were added and the whole was stirred for 2 hours at room temperature. Another portion of 1.4 parts of potassium carbonate was added. After stirring for 3 hours at 50° C., the mixture was cooled and 2.0 parts of concentrated hydrochloric acid were added. The dimethyl sulfoxide layer was evaporated. The residue was taken up in 25 parts of water and 130 parts of dichloromethane. The separated organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and methanol, saturated with ammonia, (92:4:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 20 parts of 4-methyl-2-pentanone. The product was filtered off and dried, yielding 4.4 parts (79.6%) of 5-[phenyl(1H-1,2,4-triazol-1-yl)methyl]-1H-benzotriazole; mp. 182.7° C. (compound 230).

Workup

  1. temperatureAfter cooling
  2. stirringthe whole was stirred for 2 hours at room temperature
  3. stirringAfter stirring for 3 hours at 50° C.
  4. temperaturethe mixture was cooled
  5. customThe dimethyl sulfoxide layer was evaporated
  6. customThe separated organic layer was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane, methanol and methanol
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customThe residue was crystallized from 20 parts of 4-methyl-2-pentanone
  14. filtrationThe product was filtered off
  15. customdried

Sources & evidence

ORD record
ord-abc8055151d348b1a78d6607c8cc94ff
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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