1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → n-(Bis(4-methoxyphenyl)(phenyl)methyl)-4-ethynylbenzenesulfonamide

HRID 1803811Notes

Reaction equation

HRID 1803811 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[CH:2].[C:13](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:22]1[CH:29]=[CH:28][C:25]([O:26][CH3:27])=[CH:24][CH:23]=1)[C:14]1[CH:21]=[CH:20][C:17]([O:18][CH3:19])=[CH:16][CH:15]=1>C(Cl)Cl>[CH3:27][O:26][C:25]1[CH:24]=[CH:23][C:22]([C:13]([C:14]2[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[CH:20][CH:21]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:12][S:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:8][CH:7]=2)(=[O:10])=[O:11])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 444572214-Ethynylbenzenesulfonamide

Product 1

HCID 57689141n-(Bis(4-methoxyphenyl)(phenyl)methyl)-4-ethynylbenzenesulfonamideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring slurry of 4-ethynylbenzenesulfonamide (1.81 g, 10.0 mmol) and DMTr-Cl (4.07 g, 12.0 mmol) in DCM (100 mL) was added TEA (2.8 mL). The resulting solution was allowed to stir at room temperature for overnight. Silica gel (3 g) was added to the solution followed by rotary evaporation of solvent in vacuo. The sample was absorbed onto silica gel was then loaded onto a pre-equilibrated column (with 10% TEA in hexane). Flash chromatography using 0-30% EtOAc in hexane as the gradient eluents gave the product 5 as a yellow solid (4.8 g, 99%).

Workup

  1. additionSilica gel (3 g) was added to the solution
  2. customfollowed by rotary evaporation of solvent in vacuo
  3. customThe sample was absorbed onto silica gel

Sources & evidence

ORD record
ord-20a665bc08fd4213a2735cb39239f76a
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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