Pyridine → 3'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide

HRID 325728Notes

Reaction equation

HRID 325728 reaction equation
[CH2:1]([N:8]1[C:12]([C:13](Cl)=[O:14])=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C(C([O-])=O)=NN=N1)C1C=CC=CC=1.[K+].[CH3:32][C:33]1[CH:38]=[C:37]([C:39]([CH3:41])=[O:40])[C:36]([OH:42])=[C:35]([NH2:43])[CH:34]=1.N1C=CC=CC=1>C(Cl)Cl>[C:39]([C:37]1[C:36]([OH:42])=[C:35]([CH:34]=[C:33]([CH3:32])[CH:38]=1)[NH:43][C:13]([C:12]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[N:10][N:11]=1)=[O:14])(=[O:40])[CH3:41]

Participants

6

Reactant 4

HCID 1049PyridineHCID 27564491-(3-Amino-2-hydroxy-5-methylphenyl)ethan-1-oneHCID 204638761-benzyl-1H-tetrazole-5-carbonyl chlorideHCID 23688251Potassium 1-Benzyl-1H-tetrazole-5-carboxylate

Product 1

HCID 1360453873'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of crude 1-benzyl-1H-tetrazole-5-carbonyl chloride (prepared from 0.73 g of potassium 1-benzyl-1H-tetrazole-5-carboxylate in the manner hereinbefore described in Reference Example 3) in dry methylene chloride (14 ml) was added to a stirred mixture of 3-amino-2-hydroxy-5-methylacetophenone (0.5 g) and pyridine (0.27 g) in dry methylene chloride (12 ml) at between 5° and 10° C. Stirring was maintained for 2 hours, allowing the temperature to rise to room temperature, and then the mixture was left to stand overnight. A further portion of methylene chloride (20 ml) was then added and the mixture was washed with water. The organic phase was dried over magnesium sulphate, and evaporated in vacuo to give a solid, which was recrystallised from ethanol, to give 3'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide (1.0 g), m.p. 183°-184° C.

Workup

  1. temperaturewas maintained for 2 hours
  2. customto rise to room temperature
  3. waitthe mixture was left
  4. washthe mixture was washed with water
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customevaporated in vacuo
  7. customto give a solid, which
  8. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-546e0d984c62468d83cbb73e23c50502
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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