Hydrochloric Acid → 2-chloro-4-(methylsulfonyl)-N-(1-(2-methoxyethyl)tetrazol-5-yl)-benzamide

HRID 68215Notes

Reaction equation

HRID 68215 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:15][C:16]1[N:20]([CH2:21][CH2:22][O:23][CH3:24])[N:19]=[N:18][N:17]=1.O.Cl>N1C=CC=CC=1.CC(=O)OCC>[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:15][C:16]1[N:20]([CH2:21][CH2:22][O:23][CH3:24])[N:19]=[N:18][N:17]=1)=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11128804Benzoyl chloride, 2-chloro-4-(methylsulfonyl)-HCID 583353441-(2-methoxyethyl)-1H-1,2,3,4-tetrazol-5-amine

Product 1

HCID 867235572-chloro-4-(methylsulfonyl)-N-(1-(2-methoxyethyl)tetrazol-5-yl)-benzamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

176 mg (0.75 mmol) of 2-chloro-4-(methylsulfonyl)benzoyl chloride, 145 mg (1.0 mmol) of 5-amino-1-(2-methoxyethyl)tetrazole in 2 ml of pyridine are stirred at 60° C. for 12 h. 0.1 ml of water is then added, the mixture is stirred at 60° C. for 30 min and EA and 2N HCl are added. The organic phase is separated off and washed with 2N HCl and brine, dried over Na2SO4, concentrated and purified by RP—HPLC (acetonitrile/water). Yield 66 mg (23%).

Workup

  1. customThe organic phase is separated off
  2. washwashed with 2N HCl and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by RP—HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-c8af9790b4d94610883b5f1185ffa93e
Source dataset
uspto-grants-2014_09
Patent number
US08822378B2

Reaction notes

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