Triethylamine → HCID 86587495, compound

HRID 987453Notes

Reaction equation

HRID 987453 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[C:4]([O:12][CH3:13])[C:3]=1[NH2:14].C(N([CH2:20][CH3:21])CC)C.[CH2:22]([O:29][CH2:30][C:31](Cl)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[CH2:22]([O:29][CH2:30][C:31]([NH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[C:4]([O:12][CH3:13])[C:3]=1[NH:14][C:5](=[O:10])[CH2:6][O:8][CH2:9][C:21]1[CH:20]=[CH:4][CH:3]=[CH:2][CH:7]=1)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 21891618HCID 21891618, compound

Product 1

HCID 86587495HCID 86587495, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2-Diamino-3,4,5-trimethoxybenzene (675 mg) and triethylamine (1.4 mL) were dissolved in dry dichloromethane (25 mL), benzyloxyacetyl chloride (1.34 mL) was added to the solution under ice cooling, and the mixture was stirred for 4 hours as it is. The reaction mixture was extracted with chloroform, and the resultant organic layer was washed with diluted hydrochloric acid, an aqueous solution of potassium carbonate, water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=2:3 to 1:1) to obtain the title compound.

Workup

  1. extractionThe reaction mixture was extracted with chloroform
  2. washthe resultant organic layer was washed with diluted hydrochloric acid
  3. dry with materialan aqueous solution of potassium carbonate, water and saturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=2:3 to 1:1)

Sources & evidence

ORD record
ord-377b24a2ac204efdb813b709b9a06a0f
Source dataset
uspto-grants-2003_10
Patent number
US06632810B2

Reaction notes

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