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Probenecid → 4-Dipropylsulfamoyl-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide

HRID 1060279
Notes
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Reaction equation

HRID 1060279 reaction equation
[CH2:1]([N:4]([CH2:17][CH2:18][CH3:19])[S:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH2:2][CH3:3].S(Cl)(Cl)=O.[NH2:24][C:25]1[S:26][C:27]2[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:32][CH:31]=[C:30]([O:40][CH3:41])[C:28]=2[N:29]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:17]([N:4]([CH2:1][CH2:2][CH3:3])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:24][C:25]2[S:26][C:27]3[C:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:32][CH:31]=[C:30]([O:40][CH3:41])[C:28]=3[N:29]=2)=[O:14])=[CH:15][CH:16]=1)(=[O:6])=[O:7])[CH2:18][CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4911ProbenecidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 222830262-Amino-4-methoxy-7-phenyl-benzothiazole

Product 1

HCID 222830654-Dipropylsulfamoyl-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamideYield 92%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-dipropylsulfamoyl-benzoic acid (185 mg, 0.65 mmol) in toluene (10 ml) was added thionylchloride (600 mg, 5 mmol) and the mixture heated to 80° C. for 17 h. After cooling the solvent was evaporated and the resudue was taken up in THF (20 ml), 2-amino-4-methoxy-7-phenyl-benzothiazole (128 mg, 0.5 mmol), triethylamine (105 μl, 0.75 mmol), and DMAP (6 mg, 0.05 mmol) were then added and the mixture was stirred for 1 hour at r.t. followed by 1 hour at 60° C. After cooling to r.t. the reaction mixture was quenched by addition of 10% aq. Na2CO3 solution (30 ml) and EtOAc (30 ml) and vigorous stirring. After separation of the phases the aqueous phase was extracted with EtOAc (30 ml) and the combined orgainc phases were washed with 10% aq. Na2CO3, dried with Na2SO4, filtered and evaporated. The residue was then chromatographed over SiO2 (Merck 230-400 mesh) eluting with a gradient of cyclohexane/EtOAc from (1:4) to 100% EtOAc. After pooling and evaporation of the product fractions the title compound was obtained as a white solid (240 mg, 92% yield), MS: m/e=524.2 (M+H+).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas evaporated
  3. waitfollowed by 1 hour at 60° C
  4. temperatureAfter cooling to r.t. the reaction mixture
  5. customwas quenched by addition of 10% aq. Na2CO3 solution (30 ml) and EtOAc (30 ml) and vigorous stirring
  6. customAfter separation of the phases the aqueous phase
  7. extractionwas extracted with EtOAc (30 ml)
  8. washthe combined orgainc phases were washed with 10% aq. Na2CO3
  9. dry with materialdried with Na2SO4
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was then chromatographed over SiO2 (Merck 230-400 mesh)
  13. washeluting with a gradient of cyclohexane/EtOAc from (1:4) to 100% EtOAc
  14. customevaporation of the product fractions the title compound

Sources & evidence

ORD record
ord-366761ca515c4e5086827acf8cf75c1f
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06521754B2

Reaction notes

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