Triethylamine → HCID 66989594, compound

HRID 2407716Notes

Reaction equation

HRID 2407716 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:9][NH2:10])=[O:8].[CH2:11]([O:18][CH2:19][C:20](Cl)=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][CH2:19][C:20]([NH:10][NH:9][C:7](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 255881Picolinohydrazide

Product 1

HCID 66989594HCID 66989594, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Picolinohydrazide (4.55 g) was dissolved in dichloromethane (40 mL) and 2-(benzyloxy)acetyl chloride (6.06 mL) was added slowly with cooling. Triethylamine (5.98 mL) was added slowly with a strong exotherm. Additional dichloromethane (45 mL) was added to aid stirring. The reaction was allowed to stir overnight. The reaction was partitioned between ethyl acetate and sodium hydrogen carbonate aqueous solution. The organic phase was washed with brine, dried and purified by column chromatography using an eluant of 10% ethyl acetate/dichloromethane to provide the title compound (4.1 g) having the following physical data.

Workup

  1. temperaturewith cooling
  2. stirringto stir overnight
  3. customThe reaction was partitioned between ethyl acetate and sodium hydrogen carbonate aqueous solution
  4. washThe organic phase was washed with brine
  5. customdried
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-7e7f24c06a0149e49f0c1e39d0b090a7
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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