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Tetrahydrofuran → HCID 66937363, compound

HRID 408696
Notes
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Reaction equation

HRID 408696 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1.C1COCC1.CCN(C(C)C)C(C)C.Cl[CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]>CCOC(C)=O>[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]2[N:6]([CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])[CH:7]=[N:8][C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 178486901HCID 178486901, compound

Product 1

HCID 66937363HCID 66937363, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

To a mixture of 5-chloro-6-methoxy-1H-benzoimidazole (0.320 g, 1.75 mmol) and THF (10 mL), was added DIPEA (0.850 mL, 4.9 mmol) followed by 1-chloromethoxy-2-methoxy-ethane (0.310 g, 2.45 mmol) at 23° C. After stirring for 18 h, EtOAc (50 mL) was added. The organic layer was washed with brine (20 mL), dried, filtered, and concentrated under reduced pressure to afford (0.31 g) of crude material which was used without further purification in the next reaction.

Workup

  1. washThe organic layer was washed with brine (20 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0249f952dfe64625a66a40841044fa40
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759345B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes