Hydrochloric Acid → HCID 11949832, compound

HRID 221967Notes

Reaction equation

HRID 221967 reaction equation
N1C=CC=CC=1.Cl.[NH2:8][C:9]1[CH:37]=[CH:36][C:12]([CH2:13][N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)[C:15]2=[O:35])=[CH:11][CH:10]=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>O.C1COCC1>[F:32][C:31]([F:33])([F:34])[O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][N:16]2[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:14]([CH2:13][C:12]3[CH:11]=[CH:10][C:9]([NH:8][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:37][CH:36]=3)[C:15]2=[O:35])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59707058HCID 59707058, compound

Product 1

HCID 11949832HCID 11949832, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pyridine (0.4 mL, 5.0 mmol) was added to a suspension of the hydrochloride of 1-(4-aminobenzyl)-3-(4-trifluoromethoxybenzyl)-1,3-dihydrobenzimidazol-2-one (U) (806 mg, 1.79 mmol) in abs. THF (40 mL). The reaction mixture was stirred at RT for 30 min, methanesulphonyl chloride (0.16 mL, 2.1 mmol, dissolved in abs. THF (1 mL)) was added within a period of 20 min, and the reaction mixture was again stirred at RT over a period of 18 h. To the reaction mixture there were then added H2O (150 mL) and aqueous 2N hydrochloric acid solution (5 mL). After 2 hours, the precipitated solid matter was separated by a frit and then dried in vacuo and recrystallized from ethanol (20 mL). The desired product N-{4-[3-(4-trifluoromethoxybenzyl)-2-oxo-2,3-dihydrobenzimidazol-1-ylmethyl]phenyl}methanesulfonamide (70) was obtained in a yield of 505 mg (57% of theory, mp: 182-187° C.).

Workup

  1. stirringthe reaction mixture was again stirred at RT over a period of 18 h
  2. waitAfter 2 hours
  3. customthe precipitated solid matter was separated by a frit
  4. customdried in vacuo
  5. customrecrystallized from ethanol (20 mL)

Sources & evidence

ORD record
ord-2fbc1dcacebf45558d1693377049d7f7
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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