Sodium Chloride → HCID 11949829, compound

HRID 221964Notes

Reaction equation

HRID 221964 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[C:15]([C:19]1[CH:47]=[CH:46][C:22]([CH2:23][N:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])=[CH:36][CH:35]=3)[C:25]2=O)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].[OH-].[Na+].[Na+].[Cl-]>C1(C)C=CC(C)=CC=1.O>[C:15]([C:19]1[CH:47]=[CH:46][C:22]([CH2:23][N:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])=[CH:36][CH:35]=3)[C:25]2=[S:2])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 11949831HCID 11949831, compound

Product 1

HCID 11949829HCID 11949829, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7809P-XyleneSolvent

Procedure

Phosphorus pentasulfide (300 mg, 0.67 mmol) was added to a suspension of N-{4-[3-(4-tert-butylbenzyl)-2-oxo-2,3-dihydrobenzimidazol-1-ylmethyl]phenyl}methanesulfonamide (6) (235 mg, 0.51 mmol) in para-xylene (20 mL) under a blanket of argon. The reaction mixture was heated to the boil over a period of 5 h. Following cooling, there was added to the reaction mixture water (1 mL) followed by 2N NaOH solution in water (10 mL), and the mixture was stirred at RT for 30 min. To the reaction mixture there was added aqueous NaCl solution, and the resulting mixture was extracted with ethyl acetate (4×20 mL). The combined organic phases were dried over Na2SO4 and the solvent removed in vacuo. After purifying the residue by means of column chromatography (SiO2; cyclohexane/EtOAc 7:3), the desired product N-{4-[3-(4-tert-butylbenzyl)-2-thioxo-2,3-dihydrobenzoimidazol-1-ylmethyl]phenyl}methanesulfonamide (2) (99 mg, 40% of theory, mp: 176-178° C.) was obtained.

Workup

  1. temperatureThe reaction mixture was heated to the boil over a period of 5 h
  2. temperatureFollowing cooling
  3. extractionthe resulting mixture was extracted with ethyl acetate (4×20 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customthe solvent removed in vacuo
  6. customAfter purifying the residue by means of column chromatography (SiO2; cyclohexane/EtOAc 7:3)

Sources & evidence

ORD record
ord-3116cf3221b14e588e84b1e1037f9860
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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