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Dimethylformamide → HCID 86656259, compound

HRID 221382
Notes
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Reaction equation

HRID 221382 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(Cl)(=O)C([Cl:31])=O.CN(C=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([Cl:31])=[O:24])(=[O:17])=[O:16])=[CH:11][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 250949733-(2',4'-Dichlorobiphenyl-4-ylsulfonamido)benzoic acid

Product 1

HCID 86656259HCID 86656259, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 3-(2′,4′-dichlorobiphenyl-4-ylsulfonamido)benzoic acid (1.50 g, 3.56 mmol) in DCM (35 mL) was stirred at 0° C. and oxalyl chloride (340 μL, 3.9 mmol) was added, followed by a catalytic amount of DMF (<50 μL). The mixture was allowed to warm to room temperature and stirred for two days, during which time the solid dissolved to form a light yellow clear solution. The mixture was evaporated under reduced pressure and the residue was azeotroped with toluene (3 mL), then hexane (10 mL) and the title compound obtained as a light brown, slightly gummy, solid (1.5 g) which was used without further purification.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for two days, during which time the solid
  3. dissolutiondissolved
  4. customto form a light yellow clear solution
  5. customThe mixture was evaporated under reduced pressure
  6. customthe residue was azeotroped with toluene (3 mL)

Sources & evidence

ORD record
ord-5a21c4556dd8419cb5b4b454fde0a520
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08207167B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes