Hydrochloric Acid → 3-(2',4'-Dichlorobiphenyl-4-ylsulfonamido)-N,N-dimethylbenzamide

HRID 221383Notes

Reaction equation

HRID 221383 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:22]2[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=2)[C:25](Cl)=[O:26])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[Cl-].[NH4+].Cl>C1COCC1>[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:22]2[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=2)[C:25]([N:2]([CH3:3])[CH3:1])=[O:26])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 25517Ammonium ChlorideHCID 86656259HCID 86656259, compound

Product 1

HCID 673291013-(2',4'-Dichlorobiphenyl-4-ylsulfonamido)-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 M dimethylamine in THF (5 mL) was added to 3-(2′,4′-dichlorobiphenyl-4-ylsulfonamido)benzoyl chloride (350 mg, 0.76 mmol) and the mixture was stirred at room temperature for 3 days. Saturated ammonium chloride (3 mL) was added and the solution acidified to pH 3 with 2 M HCl. The mixture was extracted with EtOAc (3×5 mL) and the organic layer was washed with brine (5 mL), dried over MgSO4, filtered and evaporated to give a yellow glass. This was triturated with acetone and the title compound obtained as a white solid (130 mg).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×5 mL)
  2. washthe organic layer was washed with brine (5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a yellow glass
  7. customThis was triturated with acetone

Sources & evidence

ORD record
ord-e94d958d8a5d4956a15d8153fc1df203
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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