Dimethylformamide → HCID 18630867, compound

HRID 1059652Notes

Reaction equation

HRID 1059652 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19].CN(C=O)C.Br[CH2:26][CH2:27][Cl:28]>O>[Cl:28][CH2:27][CH2:26][N:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:10]([CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[C:11]1=[O:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 78491-Bromo-2-ChloroethaneHCID 18630869HCID 18630869, compound

Product 1

HCID 18630867HCID 18630867, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

Into a stirred solution of 1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,3-dihydro-2H-benzimidazol-2-one (6.5 g, 25 mmoles) in DMF (40 ml) 80% sodium hydride (0.9 g, 30 mmoles) was added. After 30 minutes of stirring and heating to 35° C., 1-bromo-2-chloroethane (6.2 g, 48 mmoles) was added, the reaction temperature was increased to 90° C. and kept for 6 hours then cooled at room temperature. The reaction mixture was poured into water, extracted with diethyl ether, and the organic layer was taken to dryness. The residue was purified by flash chromatography (cyclohexane-ethyl acetate 50-50) to give 2.8 g of the title compound as a thick oil which was used without any further purification.

Workup

  1. temperaturethe reaction temperature was increased to 90° C.
  2. waitkept for 6 hours
  3. temperaturethen cooled at room temperature
  4. extractionextracted with diethyl ether
  5. customThe residue was purified by flash chromatography (cyclohexane-ethyl acetate 50-50)

Sources & evidence

ORD record
ord-33aee281c55240f7b379bd2a71ad402c
Source dataset
uspto-grants-2003_02
Patent number
US06521623B1

Reaction notes

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