5-Chlorovaleryl chloride → HCID 19599425, compound

HRID 609614Notes

Reaction equation

HRID 609614 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(C(C)C)CC)(C)C.[Cl:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](Cl)=[O:29]>C1COCC1>[Cl:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:29]

Participants

5

Reactant 3

HCID 740895-Chlorovaleryl chlorideHCID 81531DiisopropylethylamineHCID 5743383Ethyl 2-(2-aminophenyl)acetate

Product 1

HCID 19599425HCID 19599425, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-aminophenylacetate (5.60 g, 0.031 mole) and diisopropylethylamine (7.08ml, 0.042 mole) in dry THF (75ml) was treated with 5 chlorovaleryl chloride (4.00 ml, 0.031 mole) and left to stir for 1 h. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (200 ml) and washed with 1M HCl (100 ml), dried (Na2SO4) and concentrated in vacuo to afford a beige solid. This was washed with n-pentane/ether (1:1) and dried to afford the title compound as a light beige solid (8.1 g, 91%).

Workup

  1. waitleft
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate (200 ml)
  4. washwashed with 1M HCl (100 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto afford a beige solid
  8. washThis was washed with n-pentane/ether (1:1)
  9. customdried

Sources & evidence

ORD record
ord-8ab540c102cb4ead9e50e1f4c2aea780
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Reaction notes

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