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1,2-Dichloroethane → 1-Methylpyrazol-5-yl 1-Methylbenzotriazole-5-carboxylate

HRID 1263413
Notes
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Reaction equation

HRID 1263413 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[N:4]=[N:3]1.[CH3:14][N:15]1[C:19](O)=[CH:18][CH:17]=[N:16]1.C(#N)C.C(Cl)CCl>CN(C1C=CN=CC=1)C.O.C(N(CC)CC)C>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13][C:19]3[N:15]([CH3:14])[N:16]=[CH:17][CH:18]=3)=[O:12])=[CH:10][C:5]=2[N:4]=[N:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 6342AcetonitrileHCID 27765491-methyl-1H-1,2,3-benzotriazole-5-carboxylic acidHCID 178481816HCID 178481816, compound

Product 1

HCID 186160341-Methylpyrazol-5-yl 1-Methylbenzotriazole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 962WaterSolvent
HCID 8471TriethylamineSolvent

Procedure

1.5 g of 1-methylbenzotriazole-5-carboxylic acid (8.5 mmol) and 0.87 g of 1-methyl-5-hydroxypyrazole (8.9 mmol) were dissolved in 70 ml of abs. acetonitrile and admixed with 1.62 g of EDC (8.5 mmol), 2 ml of triethylamine and a catalytic amount of DMAP. After the reaction had ended, the solution was poured into water and the mixture was extracted with ethyl acetate. The organic phase was washed and dried, and the product was then purified by crystallization. Yield: 0.77 g (35%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed
  3. customdried
  4. customthe product was then purified by crystallization

Sources & evidence

ORD record
ord-65c5ee7c7cf14fd28ac87b0307fa786b
Source dataset
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06541423B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes