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

HRID 325729Notes

Reaction equation

HRID 325729 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]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([NH2:41])[C:36]=1[OH:42])=[O:34].N1C=CC=CC=1>C(Cl)Cl>[C:33]([C:35]1[C:36]([OH:42])=[C:37]([CH:38]=[CH:39][CH:40]=1)[NH:41][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:34])[CH3:32]

Participants

6

Reactant 4

HCID 1049PyridineHCID 4592943-Amino-2-hydroxyacetophenoneHCID 204638761-benzyl-1H-tetrazole-5-carbonyl chlorideHCID 23688251Potassium 1-Benzyl-1H-tetrazole-5-carboxylate

Product 1

HCID 1360663373'-acetyl-1-benzyl-2'-hydroxy-1H-tetrazole-5-carboxanilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of crude 1-benzyl-1H-tetrazole-5-carbonyl chloride (prepared from 2.4 g of potassium 1-benzyl-1H-tetrazole-5-carboxylate in the manner hereinbefore described in Reference Example 3) in dry methylene chloride (50 ml) was added to a stirred solution of 3-amino-2-hydroxyacetophenone (1.5 g) and pyridine (0.9 g) in dry methylene chloride (40 ml) at 10° C. After standing at room temperature overnight, the solution was evaporated in vacuo and the resulting solid residue was recrystallised from a large volume of ethanol to give 3'-acetyl-1-benzyl-2'-hydroxy-1H-tetrazole-5-carboxanilide (1.5 g), in the form of pale yellow needles, m.p. 155°-157° C.

Workup

  1. customthe solution was evaporated in vacuo
  2. customthe resulting solid residue was recrystallised from a large volume of ethanol

Sources & evidence

ORD record
ord-c5f53f946cc74423888f59973833ed75
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

Loading…