Toluene → HCID 11949998, compound

HRID 221956Notes

Reaction equation

HRID 221956 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([C:27]1[CH:51]=[CH:50][C:30]([CH2:31][N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])=[CH:40][CH:39]=3)[C:33]2=O)=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].C1(C)C=CC=CC=1>O>[C:23]([C:27]1[CH:51]=[CH:50][C:30]([CH2:31][N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])=[CH:40][CH:39]=3)[C:33]2=[S:10])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 11949830HCID 11949830, compound

Product 1

HCID 11949998HCID 11949998, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfide) (640 mg, 1.58 mmol) was added to a solution of N-{4-[3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-ylmethyl]phenyl}methanesulfonamide (4) (1008 mg, 2.63 mmol) in abs. toluene (30 mL). The reaction mixture was heated to the boil over a period of 5 h. The reaction mixture was then stirred overnight. Water (40 mL) was added and the mixture was extracted with chloroform (3×30 mL). The combined organic phases were washed with H2O (2×20 mL), dried over Na2SO4, and the solvent was removed in vacuo. Following purification of the residue by means of column chromatography (SiO2 (150 g); 1000 mL cyclohexane/EtOAc 4:1), the desired product N-{4-[3-(4-tert-butylbenzyl)-2-thioxoimidazolidinylmethyl]phenyl}methanesulfonamide (1) (545 mg, 52% of theory) was obtained.

Workup

  1. temperatureThe reaction mixture was heated to the boil over a period of 5 h
  2. extractionthe mixture was extracted with chloroform (3×30 mL)
  3. washThe combined organic phases were washed with H2O (2×20 mL)
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. custompurification of the residue by means of column chromatography (SiO2 (150 g); 1000 mL cyclohexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-81198f27e9be4f6f9ad9be4a8da0e3d1
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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