1-Butanol → 2-((2-(Trifluoromethyl)phenyl)formamido)acetic acid

HRID 64991Notes

Reaction equation

HRID 64991 reaction equation
[OH-:1].[Na+].[F:3][C:4]([F:15])([F:14])[C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8].[CH2:16]([OH:20])[CH2:17]CC.[NH4+:21].[OH-]>NCC(O)=O.O.C(O)(C)C>[F:3][C:4]([F:15])([F:14])[C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH:21][CH2:17][C:16]([OH:20])=[O:1])=[O:8]

Participants

8

Reactant 4

HCID 2631-ButanolHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 675612-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 167778182-((2-(Trifluoromethyl)phenyl)formamido)acetic acid

Reagents, catalysts & solvents 3

HCID 750GlycineSolventHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

In a 500 ml, 3-necked flask was dissolved glycine (9.03 g) in water (50 ml). The flask was cooled in an ice/methanol bath. Sodium hydroxide (12.6 g) in 30 cc of water was added. 2-Trifluoromethylbenzoyl chloride (25 g) was added at a temperature below 0° C. The bath was removed and the reaction mixture stirred for 2.5 hours at room temperature. To this was added concentrated HCl until the pH was 1. The solid was collected by filtration, washed with water and dried to give 25 g(84%), m.p. 147°-149° C. The product was a single spot by thin layer chromatography. (n-butyl alcohol:isopropyl alcohol:NH4OH; 10:4:4).

Workup

  1. temperatureThe flask was cooled in an ice/methanol bath
  2. customThe bath was removed
  3. additionTo this was added concentrated HCl until the pH was 1
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customdried
  7. customto give 25 g(84%), m.p. 147°-149° C

Sources & evidence

ORD record
ord-6c212c2210164fa8a5fe8c60c8c89f1c
Source dataset
uspto-grants-1986_09
Patent number
US04612185

Reaction notes

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