Ethanolamine → 4-fluoro-N-(2-hydroxyethyl)-2-nitrobenzamide

HRID 1156329Notes

Reaction equation

HRID 1156329 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=1>CC1C=CC=CC=1>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:1][CH2:2][CH2:3][OH:4])=[O:11])=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 133524084-Fluoro-2-nitrobenzoyl chloride

Product 1

HCID 202789664-fluoro-N-(2-hydroxyethyl)-2-nitrobenzamideYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred and cooled mixture of 25 parts of 2-aminoethanol and 135 parts of methylbenzene is added dropwise a solution of 29 parts of 4-fluoro-2-nitrobenzoyl chloride in methylbenzene. Upon completion, stirring is continued for 30 minutes at room temperature. The precipitated product is filtered off, taken up in water and extracted with 4-methyl-2-pentanone. The extract is dried, filtered and evaporated, yielding 28 parts (64%) of 4-fluoro-N-(2-hydroxyethyl)-2-nitrobenzamide as a residue.

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. filtrationThe precipitated product is filtered off
  4. extractionextracted with 4-methyl-2-pentanone
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-23933cabc27e40829681d62a62c64867
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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