2-Bromoethanol → 1-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

HRID 1747413Notes

Reaction equation

HRID 1747413 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.[Br:22][CH2:23][CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:22][CH2:23][CH2:24][N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:9]2[C:10]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=3[S:7][CH:8]=2)[C:13]1=[O:21]

Participants

6

Reactant 4

HCID 108982-Bromoethanol2×HCID 11776Triphenylphosphine2×HCID 5363146Diisopropyl azodicarboxylate2×HCID 594973791-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 594972451-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-oneYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (100 mg, 0.34 mmol), 2-Bromo-ethanol (0.03 mL, 0.41 mmol) and triphenylphosphine (107 mg, 0.41 mmol) in THF (2.0 mL) is added DIAD (0.082 mL, 0.41 mmol) in a dropwise manner. The mixture is stirred at room temperature for 20 hr and then another 0.03 mL of 2-Bromo-ethanol, 107 mg of triphenylphosphine and 0.08 mL of DIAD are added. The reaction is continued for another 24 hr and then the solvent is removed under vacuum and the residue is purified by flash column chromatography to give 75 mg (55%) of 1-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one.

Workup

  1. waitThe reaction is continued for another 24 hr
  2. customthe solvent is removed under vacuum
  3. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-08de1778b2d543779f3ae9e872a3a58f
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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