Water → HCID 19976898, compound

HRID 1440320Notes

Reaction equation

HRID 1440320 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9]Cl)=O)=[CH:5][CH:4]=1.[CH:13]#[C:14][CH:15]([OH:18])[CH2:16][CH3:17].C(N(CC)CC)C.[OH2:26]>C1C=CC=CC=1>[OH:18][CH:15]([C:16]1[O:26][N:9]=[C:7]([C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:17]=1)[CH2:14][CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 929811-Pentyn-3-olHCID 21579386N-Chloro-4-methoxybenzamide

Product 1

HCID 19976898HCID 19976898, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 79.8 g (43 mmol) of 4-methoxybenzhydroxamic acid chloride and 7.23 g (86 mmol) of 1-pentyn-3-ol in 160 ml of benzene, a solution of 6.53 g (64.5 mmol) of triethylamine in 80 ml of benzene was added dropwise while maintaining the internal temperature at 3°-5° C. After the mixture was stirred for 2 hours, water was added so that the reaction product was extracted in the organic layer. The organic layer was separated and collected and the solvent was distilled off, whereby an oily residue was obtained. The oily residue was purified by silica gel chromatography (eluent: 30:1 chloroform/methyl alcohol), so that the title compound was obtained as yellow oil [yield: 8.07 g (81%)].

Workup

  1. temperaturewhile maintaining the internal temperature at 3°-5° C
  2. extractionwas extracted in the organic layer
  3. customThe organic layer was separated
  4. customcollected
  5. distillationthe solvent was distilled off
  6. customwhereby an oily residue was obtained
  7. customThe oily residue was purified by silica gel chromatography (eluent: 30:1 chloroform/methyl alcohol), so that the title compound
  8. customwas obtained as yellow oil [yield: 8.07 g (81%)]

Sources & evidence

ORD record
ord-73a8b8638c4a4186938157a1a91bb58b
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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