Sodium Carbonate → 2,4-Dichloro-N-[[4-(3-thienyl)phenyl]sulfonyl]benzamide

HRID 351130Notes

Reaction equation

HRID 351130 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=1)(=[O:9])=[O:8])=[O:5].[S:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:24]2[CH:25]=[CH:26][S:22][CH:23]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])=[O:5]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 17975450HCID 17975450, compound

Product 1

HCID 179755102,4-Dichloro-N-[[4-(3-thienyl)phenyl]sulfonyl]benzamide

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(2,4-dichlorobenzoyl)-4-iodo-phenylsulfonamide (0.10 mmol) in toluene/ethanol 20/1 (3 mL) is added 3-thiopheneboronic acid (0.18 mmol, 0.18 mL, 1.0M solution in DMF) and tetrakis-(triphenylphosphine) palladium (0) (10 mol %). Then 2M aqueous Na2CO3 is added (0.3 mL) and the stirred mixture is heated to 100° C. overnight (17 hr)(Buchi Syncore system). The reaction mixture is concentrated (Genevac apparatus), then water is added (2.5 mL) and ethyl acetate (5 mL). The phases are separated and the aqueous layer is extracted with ethyl acetate (3×5 mL). This process is automatically carried out using a Tecan system. The solvents are evaporated and the corresponding crude product is purified by HPLC to give the title compound.

Workup

  1. concentrationThe reaction mixture is concentrated (Genevac apparatus)
  2. additionwater is added (2.5 mL) and ethyl acetate (5 mL)
  3. customThe phases are separated
  4. extractionthe aqueous layer is extracted with ethyl acetate (3×5 mL)
  5. customThe solvents are evaporated
  6. customthe corresponding crude product is purified by HPLC

Sources & evidence

ORD record
ord-471c68c32d7844dc97190e4fcab38a3c
Source dataset
uspto-grants-2007_02
Patent number
US07183320B2

Reaction notes

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