Oxalyl chloride → HCID 20571271, compound
Reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[Cl:7][C:8]1[C:13]([NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])=[CH:12][CH:11]=[CH:10][N:9]=1>ClCCl>[Cl:7][C:8]1[C:13]([N:14]([S:15]([C:18]([F:21])([F:19])[F:20])(=[O:17])=[O:16])[C:2]([C:1]([N:14]([C:13]2[C:8]([Cl:7])=[N:9][CH:10]=[CH:11][CH:12]=2)[S:15]([C:18]([F:19])([F:20])[F:21])(=[O:16])=[O:17])=[O:5])=[O:3])=[CH:12][CH:11]=[CH:10][N:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Oxalyl chloride (0.762 gram; 0.006 mole) is added dropwise to a suspension of N-(2-chloro-3-pyridyl)-trifluoromethanesulfonamide (2.61 grams; 0.01 mole) and powdered Type 3A molecular sieves (5.0 grams) in dichloromethane (75 mls) at 0° C. under a nitrogen atmosphere. The mixture is then heated to 60° C., held thereat for 3 hours, and then stirred at room temperature for 60 hours. The reaction mixture is filtered and the filtrate is evaporated to dryness. The resulting residue is extracted with diethyl ether, and the combined ethereal extracts are dried over anhydrous sodium sulfate. The dried ethereal extract is then separated and evaporated to obtain 2.33 grams (81% of theoretical) of crude product.
Workup
- customat 0° C.
- filtrationThe reaction mixture is filtered
- customthe filtrate is evaporated to dryness
- extractionThe resulting residue is extracted with diethyl ether
- dry with materialthe combined ethereal extracts are dried over anhydrous sodium sulfate
- extractionThe dried ethereal extract
- customis then separated
- customevaporated
- customto obtain 2.33 grams (81% of theoretical) of crude product
Sources & evidence
- ORD record
- ord-1ac0154a45b94948ae720e94f5ed487d
- Source dataset
- uspto-grants-1981_09
- Patent number
- US04288592
Reaction notes
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