Triethylamine → HCID 15662259, compound

HRID 2247991Notes

Reaction equation

HRID 2247991 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:13](Cl)(=O)[CH:14]([CH3:16])[CH3:15].C(N(CC)CC)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(OCC)(=O)C.C1(C)C(C)=CC=CC=1>[CH:14]([C:16]1[O:12][C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[N:1]=1)([CH3:15])[CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 62325Isobutyryl chlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 15662259HCID 15662259, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-amino-4-hydroxybenzoate (5.00 g, 29.9 mmol), isobutyryl chloride (3.51 g, 32.9 mmol), triethylamine (3.33 g, 32.9 mmol), pyridinium p-toluenesulfonate (2.5 g, 10 mmol) and xylene (100 mL) was heated to reflux overnight and then cooled to room temperature. The reaction was diluted with ethyl acetate (100 mL) and washed with water (2×50 mL), dried with magnesium sulfate, filtered and concentrated to give the title compound (6.82 g, quantitative yield) as a brown oil. Also prepared by this method were:

Workup

  1. temperatureto reflux overnight
  2. washwashed with water (2×50 mL)
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a05e15a2151b420cba35bb2129fea7c7
Source dataset
uspto-grants-1991_08
Patent number
US05037842

Reaction notes

Loading…