Pyridine → N-(2-methyltetrazol-5-yl)-2,2-diphenylacetamide

HRID 2184964Notes

Reaction equation

HRID 2184964 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][N:5]([CH3:7])[N:6]=1.N1C=CC=CC=1.[C:14]1([CH:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:7][N:5]1[N:4]=[N:3][C:2]([NH:1][C:21](=[O:22])[CH:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:6]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 746372,2-Diphenylacetyl chlorideHCID 1386772-methyl-2H-1,2,3,4-tetrazol-5-amineHCID 516892Sodium Bicarbonate

Product 1

HCID 662625N-(2-methyltetrazol-5-yl)-2,2-diphenylacetamideYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-amino-2-methyl-2H-tetrazole (0.50 g, 5.05 mmol), pyridine (0.48 g, 6.06 mmol) and DMAP (0.06 g, 0.51 mmol) in dichloromethane (30 ml) was added at 0° C. diphenylacetyl chloride (1.16 g, 5.05 mmol). Stirring was continued at RT for 2 h, the reaction mixture was poured into sat. NaHCO3 solution (50 ml) and extracted with dichloromethane (3×50 ml). The combined organic layers were washed with brine (70 ml), dried (Na2SO4) and evaporated. The crude product was crystallized from ethyl acetate/hexane to give the title compound (0.83 g, 56%) as a white solid, m.p. 218° C. (dec.) and MS: m/e=293.1 (M+H+).

Workup

  1. extractionextracted with dichloromethane (3×50 ml)
  2. washThe combined organic layers were washed with brine (70 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe crude product was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-699e45e125f64270bc2230268167225e
Source dataset
uspto-grants-2002_06
Patent number
US06399641B1

Reaction notes

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