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

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Water	HCID 962	—
Reactant	Benzoyl chloride, 2-chloro-4-(methylsulfonyl)-	HCID 11128804	—
Reactant	1-(2-methoxyethyl)-1H-1,2,3,4-tetrazol-5-amine	HCID 58335344	—
Solvent	Pyridine	HCID 1049	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-chloro-4-(methylsulfonyl)-N-(1-(2-methoxyethyl)tetrazol-5-yl)-benzamide	HCID 86723557	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

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%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08822378B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-c8af9790b4d94610883b5f1185ffa93e
Source note	uspto-grants-2014_09