Dimethylformamide → HCID 59632099, compound

HRID 2369079Notes

Reaction equation

HRID 2369079 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([C:28](O)=[O:29])=[N:9]1.CN(C=O)C.C(Cl)(=O)C([Cl:39])=O.O1CCOCC1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([C:28]([Cl:39])=[O:29])=[N:9]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 312751,4-DioxaneHCID 65578Oxalyl chloride2×HCID 59631853HCID 59631853, compound

Product 1

HCID 59632099HCID 59632099, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 1-(2-chlorophenyl)-5-(5-(3-(methylsulfonyl)phenyl)thiophen-2-yl)-1H-pyrazole-3-carboxylic acid (160 mg, 0.35 mmol) in PhH (1.0 mL) was added a small amount of DMF. Oxalyl chloride (60 μL, 0.69 mmol) was added to the suspension. After stirring for 15 minutes at ambient temperature, gas evolution had ceased and only part of the solids had dissolved. After 25 minutes dioxane (2.0 mL) was added. There was renewed gas evolution and most of the solids dissolved. After 30 minutes additional oxalyl chloride (50 μL, 0.57 mmol) was added. There was vigorous gas evolution and after a total of 90 minutes stirring the reaction mixture was concentrated under reduced pressure to afford 1-(2-chlorophenyl)-5-(5-(3-(methylsulfonyl)phenyl)thiophen-2-yl)-1H-pyrazole-3-carbonyl chloride as a pale brown foam. This material was carried on to the subsequent acylation without purification.

Workup

  1. dissolutiononly part of the solids had dissolved
  2. dissolutionmost of the solids dissolved
  3. stirringafter a total of 90 minutes stirring the reaction mixture
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-9f29152808044837973e547ec1135212
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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