Hydrochloric Acid → 1-benzyl-2'-benzyloxy-3'-methoxy-5'-methyl-1H-tetrazole-5-carboxanilide

HRID 325732Notes

Reaction equation

HRID 325732 reaction equation
[CH2:1]([O:8][C:9]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([CH3:18])=[CH:12][C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([N:26]1[C:30]([C:31]([O-])=[O:32])=[N:29][N:28]=[N:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[K+].C1(N=C=NC2CCCCC2)CCCCC1.Cl>N1C=CC=CC=1>[CH2:19]([N:26]1[C:30]([C:31]([NH:11][C:10]2[CH:12]=[C:13]([CH3:18])[CH:14]=[C:15]([O:16][CH3:17])[C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:32])=[N:29][N:28]=[N:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 135961882-Benzyloxy-3-methoxy-5-methylanilineHCID 23688251Potassium 1-Benzyl-1H-tetrazole-5-carboxylate

Product 1

HCID 135961251-benzyl-2'-benzyloxy-3'-methoxy-5'-methyl-1H-tetrazole-5-carboxanilideYield 3.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-benzyloxy-3-methoxy-5-methylaniline (2.6 g), potassium 1-benzyl-1H-tetrazole-5-carboxylate (2.5 g) and dicyclohexylcarbodiimide (2.1 g) in dry pyridine (100 ml) was stirred at room temperature overnight. The mixture was then poured into a mixture of ice (250 g) and concentrated hydrochloric acid (100 ml), and the mixture was allowed to stand for 1 hour. The precipitate was filtered off and recrystallised from ethanol to give 1-benzyl-2'-benzyloxy-3'-methoxy-5'-methyl-1H-tetrazole-5-carboxanilide (0.16 g), m.p. 181°-183° C.

Workup

  1. waitto stand for 1 hour
  2. filtrationThe precipitate was filtered off
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-ba001c7f8eba4c549cc3dd1f662053fa
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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