Triethylamine → HCID 20081761, compound

HRID 1609537Notes

Reaction equation

HRID 1609537 reaction equation
C([N:3](CC)CC)C.[NH2:8][C:9]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O.[C:19](Cl)(=[O:23])[CH:20]([CH3:22])[CH3:21].C(=O)([O-])[O-].[NH4+].[NH4+]>CN(C=O)C.CN(C1C=CC=CN=1)C>[C:19]([NH:8][C:9]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:3])=[O:13])(=[O:23])[CH:20]([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 781012-Amino-3-methylbenzoic acidHCID 517111Ammonium Carbonate

Product 1

HCID 20081761HCID 20081761, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dimethylaminopyridine (15 mg) followed by triethylamine (4.14 mL, 0.0279 mol) were added to a stirred solution of 2-amino-3-methylbenzoic acid (1.50 g, 0.0099 mol) in DMF (15 mL) under nitrogen at 0° C. The iso-butyryl chloride (2.07 mL, 0.0198 mol) was added dropwise then the mixture stirred at 0° C. for 30 min. followed by 30 min. at room temperature then at 120° C. for 1 hr. The suspension was then stirred at room temperature for 2 days. Ammonium carbonate (3.5 g) was added in portions and the mixture heated at 120° C. for 3 hr. After cooling to room temperature the mixture was poured into ice/water and extracted with ethyl acetate (3 times). The combined organic phase was washed with water, brine, dried (magnesium sulfate) and the solvent removed in vacuo to leave a cream solid. Recrystallisation (1:1 ethyl acetate/hexane) afforded 2-(iso-butyryl)amino-3-methylbenzamide (739 mg, 34%).

Workup

  1. waitfollowed by 30 min. at room temperature
  2. waitat 120° C. for 1 hr
  3. stirringThe suspension was then stirred at room temperature for 2 days
  4. temperaturethe mixture heated at 120° C. for 3 hr
  5. temperatureAfter cooling to room temperature the mixture
  6. extractionextracted with ethyl acetate (3 times)
  7. washThe combined organic phase was washed with water, brine
  8. dry with materialdried (magnesium sulfate)
  9. customthe solvent removed in vacuo
  10. customto leave a cream solid
  11. customRecrystallisation (1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f474c76ae46540ba81fb9f9a03a3f106
Source dataset
uspto-grants-1995_03
Patent number
US05401745

Reaction notes

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