Diethyl Ether → Ethyl 2-amino-2-(4-fluorobenzoyloxyimino)acetate

HRID 54539

Reaction equation

HRID 54539 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12](=[N:18]O)[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N=C=NCCCN(C)C)C.C(OCC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH2:18][C:12](=[N:11][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 99734-Fluorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Product 1

HCID 54483830Ethyl 2-amino-2-(4-fluorobenzoyloxyimino)acetateYield 88.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-fluorobenzoic acid (2.0 g), ethyl 2-amino-2-hydroxyiminoacetate (2.07 g) and 4-dimethylaminopyridine (0.52 g) in methylene chloride (30 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.87 ml) at 0° C. under stirring. After stirring at ambient temperature for 1 hour, diethyl ether (10 ml) was added thereto and the resulting precipitate was filtered off, washed with diethyl ether, and dried in vacuo to give ethyl 2-amino-2-(4-fluorobenzoyloxyimino)acetate (3.2 g).

Workup

  1. stirringAfter stirring at ambient temperature for 1 hour
  2. filtrationthe resulting precipitate was filtered off
  3. washwashed with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2c9c36b844f840168efb45e7c85bf2f9
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Linked notes

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