2-Amino-3-chlorobenzoic acid → 3-Chloro-N-(1-propyl-1H-tetrazol-5-yl)benzamide

HRID 872259Notes

Reaction equation

HRID 872259 reaction equation
N[C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([N:15]1[C:19]([NH2:20])=[N:18][N:17]=[N:16]1)[CH2:13][CH3:14]>>[Cl:11][C:10]1[CH:2]=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([NH:20][C:19]1[N:15]([CH2:12][CH2:13][CH3:14])[N:16]=[N:17][N:18]=1)=[O:6]

Participants

3

Reactant 2

HCID 808072-Amino-3-chlorobenzoic acidHCID 2206221-propyl-1H-tetrazol-5-amine

Product 1

HCID 9657943-Chloro-N-(1-propyl-1H-tetrazol-5-yl)benzamideYield 65%

Procedure

Employing 0.25 g (1.5 mmol) of 2-amino-3-chlorobenzoic acid and 0.19 g (1.5 mmol) of 1-propyl-1H-tetrazol-5-amine in the procedure described above and elution with CH2Cl2/MeOH/Et3N (9.4:0.3:0.3) gave the product in 65% yield.

Workup

  1. washelution with CH2Cl2/MeOH/Et3N (9.4:0.3:0.3)
  2. customgave the product in 65% yield

Sources & evidence

ORD record
ord-28b0f5264d2543ba968aa6c209411110
Source dataset
uspto-grants-2015_03
Patent number
US08975288B2

Reaction notes

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