Tetrahydrofuran → n-(2-(1,3-Dioxolan-2-yl)-4-methoxyphenyl)ethoxycarboxamide

HRID 639353Notes

Reaction equation

HRID 639353 reaction equation
ClC([O:4][CH2:5][CH3:6])=O.[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1N.C([N:23]([CH2:26]C)CC)C.C1C[O:31]CC1>>[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[CH2:6][CH2:5][O:4][NH:23][CH:26]=[O:31]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 153389082-(1,3-Dioxolan-2-yl)-4-methoxyaniline

Product 1

HCID 131728036n-(2-(1,3-Dioxolan-2-yl)-4-methoxyphenyl)ethoxycarboxamide

Procedure

Ethyl chloroformate (1.2 eq) was added to 2-(1,3-dioxolan-2-yl)-4-methoxyphenylamine (1eq) and triethyl amine (1.2 eq) in THF at 0° C. The reaction was completed instantaneously. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried and concentrated to give N-(2-(1,3-dioxolan-2-yl)-4-methoxyphenyl)ethoxycarboxamide as a yellow solid in quantitative yield.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-319bb24a285f455989ec0ff3895bfdf0
Source dataset
uspto-grants-2010_04
Patent number
US07691866B2

Reaction notes

Loading…