Ethyl bromoacetate → HCID 178519465, compound

HRID 2166045Notes

Reaction equation

HRID 2166045 reaction equation
O[N:2]1[C:6]2[CH:7]=[C:8]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[OH:12])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[H-].[Na+].[H][H].BrCC(OCC)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:13]1([CH:11]([C:8]2[CH:9]=[CH:10][C:5]3[NH:4][N:3]=[N:2][C:6]=3[CH:7]=2)[OH:12])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 149906211-hydroxy-alpha-phenyl-1H-benzotriazole-6-methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 178519465HCID 178519465, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 5.2 parts of 1-hydroxy-α-phenyl-1H-benzotriazole-6-methanol in 30 parts of dimethyl sulfoxide were added 0.96 parts of a sodium hydride dispersion 50%. The reaction mixture was stirred till no more hydrogen escapted. After the addition of 3.34 parts of ethyl 2-bromoacetate, the whole was stirred for 30 minutes at room temperature. 1.38 Parts of potassium carbonate were added and stirring was continued for 3 hours at 50° C. The dimethyl sulfoxide layer was evaporated and the residue was taken up in water and 20 parts of a hydrochloric acid solution 1N. The product was extracted with a mixture of trichloromethane and methanol (90:10 by volume). The extract was dried, filtered and concentrated. The concentrate was crystallized from 32.5 parts of dichloromethane. The product was filtered off and dried, yielding 3.1 parts (68.8%) of α-phenyl-1H-benzotriazole-5-methanol; mp. 143.0° C. (int. 70).

Workup

  1. stirringstirring
  2. waitwas continued for 3 hours at 50° C
  3. customThe dimethyl sulfoxide layer was evaporated
  4. extractionThe product was extracted with a mixture of trichloromethane and methanol (90:10 by volume)
  5. customThe extract was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was crystallized from 32.5 parts of dichloromethane
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-63f9a25f74f148f2b198e5698c6f4d83
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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