2-Amino-5-Nitrophenol → 2-(3-Chloro-2,2,3-trifluoro-propionamido)-5-nitrophenol

HRID 1759584Notes

Reaction equation

HRID 1759584 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[OH:15].[Cl:16][CH:17]([F:24])[C:18]([F:23])([F:22])[C:19](Cl)=[O:20]>Cl>[Cl:16][CH:17]([F:24])[C:18]([F:23])([F:22])[C:19]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[OH:15])=[O:20]

Participants

5

Reactant 3

HCID 49847212-Amino-5-NitrophenolHCID 6451240Aluminum(III) ChlorideHCID 141224163-Chloro-2,2,3-trifluoro-propionyl chloride

Product 1

HCID 205313262-(3-Chloro-2,2,3-trifluoro-propionamido)-5-nitrophenol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
20 °C

Procedure

146.8 g (1.1 mole) of anhydrous aluminium chloride were added with stirring to a suspension of 154 g (1 mole) of 2-amino-5-nitrophenol. The brownish black solution was cooled down to 20° C. In 20 min 181 g (1 mole) of 3-chloro-2,2,3-trifluoro-propionyl chloride were added thereto, the temperature being kept at 30° C. by cooling. After 3 hours of stirring at room temperature the solution was poured out in 2 l of icewater and 200 ml of concentrated hydrochloric acid. Stirring was continued for 1 hour. The precipitate was collected and rinsed with water until free from acid.

Workup

  1. custombeing kept at 30° C.
  2. temperatureby cooling
  3. stirringStirring
  4. waitwas continued for 1 hour
  5. customThe precipitate was collected
  6. washrinsed with water until free from acid

Sources & evidence

ORD record
ord-2109ca5a8c37471d8db0071d304d300d
Source dataset
uspto-grants-1982_07
Patent number
US04341864

Reaction notes

Loading…