Sodium Hydroxide → HCID 11949833, compound

HRID 221968Notes

Reaction equation

HRID 221968 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[F:15][C:16]([F:48])([F:47])[O:17][C:18]1[CH:46]=[CH:45][C:21]([CH2:22][N:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[N:25]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:35][CH:34]=3)[C:24]2=O)=[CH:20][CH:19]=1.[OH-].[Na+]>C1(C)C=CC(C)=CC=1.O>[F:15][C:16]([F:48])([F:47])[O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][N:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[N:25]([CH2:32][C:33]3[CH:34]=[CH:35][C:36]([NH:39][S:40]([CH3:43])(=[O:41])=[O:42])=[CH:37][CH:38]=3)[C:24]2=[S:2])=[CH:45][CH:46]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 11949832HCID 11949832, compound

Product 1

HCID 11949833HCID 11949833, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7809P-XyleneSolvent

Procedure

Phosphorus pentasulfide (444 mg, 1.0 mmol) was added to a suspension of N-{4-[3-(4-trifluoromethoxybenzyl)-2-oxo-2,3-dihydrobenzimidazol-1-ylmethyl]phenyl}methanesulfonamide (7) (300 mg, 0.61 mmol) in para-xylene (20 mL) under a blanket of argon. The reaction mixture was heated to the boil over a period of 10 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. The reaction 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 2:1), the desired product N-{4-[3-(4-trifluoromethoxybenzyl)-2-thioxo-2,3-dihydrobenzimidazol-1-ylmethyl]phenyl}methanesulfonamide (8) (162 mg, 52% of theory, mp: 167-170° C.) was obtained. After recrystallizing from methanol, there were obtained crystals having a melting point of 175-179° C.

Workup

  1. temperatureThe reaction mixture was heated to the boil over a period of 10 h
  2. temperatureFollowing cooling
  3. extractionThe reaction 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 2:1)

Sources & evidence

ORD record
ord-29e0dac52bea4bf9998181f33c8a62f7
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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