2-Methylbenzenesulfonamide → HCID 18971765, compound

HRID 2395413Notes

Reaction equation

HRID 2395413 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](O)=[O:16])=[CH:11][CH:10]=2)=[CH:5][C:4]=1[O:18][CH:19]([CH3:29])[CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN(C1C=CC=CN=1)C.[C:39]1([CH3:49])[C:40]([S:45]([NH2:48])(=[O:47])=[O:46])=[CH:41][CH:42]=[CH:43][CH:44]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:49][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[S:45]([NH:48][C:15]([C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:18][CH:19]([CH3:29])[CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:5]=2)=[CH:10][CH:11]=1)=[O:16])(=[O:47])=[O:46]

Participants

6

Reactant 4

HCID 69242-MethylbenzenesulfonamideHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 18971800HCID 18971800, compound

Product 1

HCID 18971765HCID 18971765, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acid 4'-methoxy-3'-(1-methyl-4-phenylbutoxy)-(±)[1,1'-biphenyl]-4-carboxylic acid, (0.257 g, 0.658 mmoles) in 10 ml of anhydrous methylene chloride under hydrogen atmosphere was added dimethylamino pyridine (88.46 mg, 0.728 mmoles); o-Toluenesulfonamide (0.122 g, 0.712 mmoles) and dicyclohexylcarbodiimide (0.124 g, 0.6 mmoles) the reaction mixture allowed to stir for 50 hours. The solvent was evaporated and the resulting solid triturated with methylene chloride:ether (~1:1) which lead to precipitation of by-product DCU which was filtered. Concentration of the mother liquor followed by 3 g additional triturations with ethyl acetate/ether (~1:1) caused additional deposit of white solid which was filtered. The clear filtrate was concentrated and purified on a silica gel column using methylene chloride/methanol as eluant (95:5). Concentration of fractions containing desired products gave a total of 0.37 g of white foamy solid. Recrystallization from ethyl acetate/hexane gave 0.208 grams of white solid. M.P.: 97°-100° C.

Workup

  1. customThe solvent was evaporated
  2. customthe resulting solid triturated with methylene chloride:ether (~1:1) which
  3. customlead to precipitation of by-product DCU which
  4. filtrationwas filtered
  5. filtrationwas filtered
  6. concentrationThe clear filtrate was concentrated
  7. custompurified on a silica gel column
  8. additionConcentration of fractions containing desired products

Sources & evidence

ORD record
ord-038167dc56934d5d816153d1108ad8c4
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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