Ethanolamine → HC Yellow no. 13

HRID 2050278Notes

Reaction equation

HRID 2050278 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][CH2:16][CH2:17][OH:18]>C(O)CCC>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[NH:15][CH2:16][CH2:17][OH:18])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene

Product 1

HCID 2799157HC Yellow no. 13

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 50 parts of 1-chloro-2-nitro-4-(trifluoromethyl)benzene, 37 parts of 2-aminoethanol and 100 parts of 1-butanol is stirred and refluxed overnight. The reaction mixture is cooled and evaporated. The residue is taken up in a diluted hydrochloric acid solution. The product is extracted with methylbenzene. The layers are separated and the aqueous phase is extracted with methylbenzene. The combined methylbenzene-phases are washed successively with a diluted hydrochloric acid solution and twice with water, dried, filtered and evaporated. The solid residue is crystallized from petroleumether. The product is filtered off and dried, yielding 2-{[2-nitro-4-(trifluoromethyl)phenyl]amino}ethanol; mp. 74.9° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customevaporated
  4. extractionThe product is extracted with methylbenzene
  5. customThe layers are separated
  6. extractionthe aqueous phase is extracted with methylbenzene
  7. washThe combined methylbenzene-phases are washed successively with a diluted hydrochloric acid solution and twice with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe solid residue is crystallized from petroleumether
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-1471b0bf3edb4903ae3e4b7e960a4473
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

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