Dimethyl Sulfoxide → HCID 21876992, compound

HRID 2121031Notes

Reaction equation

HRID 2121031 reaction equation
C[C:2]([CH3:5])([O-])C.[K+].C(S([NH:12][C:13]1[CH:26]=[CH:25][C:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1)(=O)=O)C.CI.[OH2:29].C[S:31]([CH3:33])=[O:32]>>[CH2:2]([S:31]([CH2:33][NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)=[CH:25][CH:26]=1)(=[O:29])=[O:32])[CH3:5]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 6328Methyl iodideHCID 21876990HCID 21876990, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21876992HCID 21876992, compoundYield 66%

Procedure

Solid potassium tert-butoxide (113 mg, 1 mmol) was added to a solution of 4-(4-ethanesulfonylaminobenzyl)-phenylamine (290 mg) (prepared as described in Example 7) in dimethyl sulfoxide (2 mL). The mixture was stirred and methyl iodide (0.1 mL, 1.5 mmol) was added. After 1 hour, the reaction mixture was poured into water and extracted with diethyl ether (2×). The organic phase was dried on potassium carbonate, evaporated and chromatographed on silica gel, eluting with dichloromethane/acetone, to give 4-[4-(ethanesulfonyl)methylaminobenzyl]-phenylamine (200 mg, 66%) as a yellow solid.

Workup

  1. extractionextracted with diethyl ether (2×)
  2. customThe organic phase was dried on potassium carbonate
  3. customevaporated
  4. customchromatographed on silica gel
  5. washeluting with dichloromethane/acetone

Sources & evidence

ORD record
ord-96e5e45550fb4e35851a3e4bb26735e8
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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