Hydrochloric Acid → 2-(3-Chloro-2,2,3-trifluoropropionamido)-5-[2-(2,4-di-tert-pentylphenoxy)-butyramido]-phenol

HRID 1759586

Reaction equation

HRID 1759586 reaction equation
[C:1]([C:6]1[CH:18]=[C:17]([C:19]([CH2:22][CH3:23])([CH3:21])[CH3:20])[CH:16]=[CH:15][C:7]=1[O:8][CH:9]([CH2:13][CH3:14])[C:10](Cl)=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2].[Cl:24][CH:25]([F:40])[C:26]([F:39])([F:38])[C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][C:31]=1[OH:37])=[O:28].N1C2C(=CC=CC=2)C=CC=1.Cl>O1CCOCC1>[Cl:24][CH:25]([F:40])[C:26]([F:38])([F:39])[C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:10](=[O:11])[CH:9]([O:8][C:7]2[CH:15]=[CH:16][C:17]([C:19]([CH2:22][CH3:23])([CH3:21])[CH3:20])=[CH:18][C:6]=2[C:1]([CH2:4][CH3:5])([CH3:3])[CH3:2])[CH2:13][CH3:14])=[CH:32][C:31]=1[OH:37])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 1703932-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chlorideHCID 205313242-(3-Chloro-2,2,3-trifluoropropionamido)-5-aminophenol

Product 1

HCID 205313212-(3-Chloro-2,2,3-trifluoropropionamido)-5-[2-(2,4-di-tert-pentylphenoxy)-butyramido]-phenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 33.85 g (0.1 mole) of 2-(2,4-di-tert-pentylphenoxy)butyryl chloride in 80 ml of dioxan was added to a solution of 26.85 g (0.1 mole) of 2-(3-chloro-2,2,3-trifluoropropionamido)-5-aminophenol and 23.7 ml (0.2 mole) of quinoline in 500 ml of dioxan at room temperature. The mixture was stirred for 90 minutes and left standing overnight. Next it was poured out in 2 l of icewater and 100 ml of concentrated hydrochloric acid. The sticky residue was extracted with ether, rinsed with water until free from acid, and dried. The solvent was evaporated and the residue recrystallized from hexane.

Workup

  1. waitleft
  2. waitstanding overnight
  3. extractionThe sticky residue was extracted with ether
  4. washrinsed with water until free from acid
  5. customdried
  6. customThe solvent was evaporated
  7. customthe residue recrystallized from hexane

Sources & evidence

ORD record
ord-a5866f60b69b4438a7eb715e4469aa46
Source dataset
uspto-grants-1982_07
Patent number
US04341864

Linked notes

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