Sodium Hydroxide → HCID 59497515, compound

HRID 1747343Notes

Reaction equation

HRID 1747343 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]3=[O:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:22]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH2:23].[OH-].[Na+].[NH4+].[Cl-]>C1COCC1.O>[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[N:14]([CH2:23][CH2:22][S:24]([NH2:27])(=[O:26])=[O:25])[C:13]3=[O:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 520075Vinyl sulfonamideHCID 594973791-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 59497515HCID 59497515, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To the solution of 1-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (50 mg, 0.17 mmol) in THF (1.0 mL) are added ethenesulfonic acid amide (40 mg, 0.34 mmol) and solid NaOH (14 mg, 0.34 mmol). The mixture is warmed up to 65° C. for 24 hr and then saturated NH4Cl solution (5.0 mL) is added along with water (5.0 mL). The mixture is extracted with EtOAc (3×20 mL). The organic layers are combined, dried (Na2SO4) and concentrated to give crude product. Purification by preparative TLC using 4% MeOH in CH2Cl2 affords 31 mg (46%) of 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid amide. LCMS (ESMS): m/z 402.10 (M+H+).

Workup

  1. extractionThe mixture is extracted with EtOAc (3×20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by preparative TLC

Sources & evidence

ORD record
ord-510f710833564f0eb1118b1a59e4630a
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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