Triphenylphosphine → 1-Isopropenyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

HRID 1747321Notes

Reaction equation

HRID 1747321 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])=[CH2:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:33][C:34]1[C:42]2[C:41]([CH2:43]O)=[CH:40][S:39][C:38]=2[CH:37]=[CH:36][CH:35]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:43][C:41]2[C:42]3[C:34]([CH3:33])=[CH:35][CH:36]=[CH:37][C:38]=3[S:39][CH:40]=2)[C:5]1=[O:13])([CH3:3])=[CH2:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 11148058(4-Methylbenzo[b]thiophen-3-yl)methanol

Product 1

HCID 594974271-Isopropenyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-oneYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-isopropenylbenzimidazolone (500 mg, 2.8 mmol) in dry THF (40 mL) are added triphenylphosphine (902 mg, 3.4 mmol) and (4-Methyl-benzo[b]thiophen-3-yl)-methanol (563 mg, 3.2 mmol). Then diisopropyl azodicarboxylate (0.70 mL, 3.4 mmol) is added drop wise into the above solution after it is cooled down to 0° C. The mixture is then stirred at room temperature for 5 hr and then the solvent is removed under vacuum and the residue is purified by flash column chromatography using gradient EtOAc/Hexane from 0% to 20% to give 630 mg (66%) of 1-isopropenyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one.

Workup

  1. customthe solvent is removed under vacuum
  2. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-5e10263d3f2644a0b15303bb5899dc22
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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