Acetyl chloride → HCID 58964491, compound

HRID 2069286Notes

Reaction equation

HRID 2069286 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([NH:10][CH3:11])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH2:16].[C:18](Cl)(=[O:20])[CH3:19]>O1CCOCC1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]([C:18](=[O:20])[CH3:19])[CH3:11])[C:7]([C:12]([F:14])([F:13])[F:15])=[CH:6][C:5]=1[NH2:16]

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 58964515HCID 58964515, compound

Product 1

HCID 58964491HCID 58964491, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Amino-5-methylamino-4-trifluoromethyl-benzoic acid methyl ester (26 mg, 0.96 mmoles) is dissolved in dioxane and after addition of acetyl chloride (54 μL, 1 eq.) the mixture is stirred for 2 h (TLC control) at 80° C. Acetyl chloride (0.9 eq.) is then added and stirring continued for 18 hours at 80° C. The mixture is evaporated to dryness. The residue is dissolved in dichloromethane, filtrated, evaporated and dried under HV. The crude product is purified by flash-chromatography (gradient hexane to ethyl acetate, silicagel) to yield 5-(acetyl-methyl-amino)-2-amino-4-trifluoromethyl-benzoic acid methyl ester as a yellow solid (36 mg, 12.8% yield) (MH+291, Rt 5.0 min.). The other monoacetyl derivative (50 mg) and the diacetyl derivative (92 mg) are also isolated.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours at 80° C
  3. customThe mixture is evaporated to dryness
  4. dissolutionThe residue is dissolved in dichloromethane
  5. filtrationfiltrated
  6. customevaporated
  7. customdried under HV
  8. customThe crude product is purified by flash-chromatography (gradient hexane to ethyl acetate, silicagel)

Sources & evidence

ORD record
ord-6ccfd62618c9468eab03e3760ae5004f
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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