Hydrochloric Acid → 1-(2,4-dichlorophenyl)-4-methyl-5-(4-iodophenyl)-N-(1,1-dioxothiomorpholino)-1H-pyrazole-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	4-Amino-1lambda~6~,4-thiazinane-1,1-dione	HCID 12708263	—
Reactant	1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid	HCID 66761205	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	1-(2,4-dichlorophenyl)-4-methyl-5-(4-iodophenyl)-N-(1,1-dioxothiomorpholino)-1H-pyrazole-3-carboxamide	HCID 46912920	31.4%

Reaction Steps

The acid (7.5 g, 15.8 mmol) obtained from step D was taken in a 500 ml 1 neck flask equipped with a nitrogen inlet and to it 200 ml of DCM, 4-aminothiomorpholine-1,1-dioxide (2.61 g, 17.4 mmol), TBTU (5.59 g, 17.4 mmol) and DIPEA (2.25 g, 17.4 mmol) were added and the contents were stirred for 1 hour. To the reaction mixture, 100 ml of water was added and the contents were acidified to pH ˜2 using concentrated HCl. The organic layer was separated, washed with brine, dried over sodium sulphate and concentrated to give the amide (3 g, 31.2%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853205B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-7009af71a4514617bd6ef1f444e1726c
Source note	uspto-grants-2014_10