Ethyl isocyanate → HCID 15885811, compound

HRID 1603005Notes

Reaction equation

HRID 1603005 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].C(=O)(O)[O-].[Na+].[CH2:17]([N:19]=[C:20]=[O:21])[CH3:18]>O1CCOCC1.O.O>[CH2:17]([NH:19][C:20]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5])=[O:21])[CH3:18]

Participants

6

Reactant 3

HCID 8022Ethyl isocyanateHCID 1512106-Methylanthranilic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 15885811HCID 15885811, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To an ice cooled solution of 2-amino-6-methylbenzoic acid (500 mg, 3.3 mmol) and sodium bicarbonate (277 mg, 3.3 mmol) in 9 mL of dioxane/water (2:1) was added ethyl isocyanate (281 mg, 3.96 mmol). The reaction was slowly warmed to room temperature while stirring overnight. The reaction mixture was diluted with water and extracted with EtOAc. The aqueous fraction was acidified with 2N HCl and extracted with EtOAc. The organic fraction was dried (MgSO4), filtered, and evaporated under reduced pressure affording 272 mg of 2-[[(ethylamino)carbonyl]amino]-6-methylbenzoic acid used directly in the next reaction: 1H-NMR (300 MHz, d6 -DMSO) δ 1.02 (t, J=7 Hz, 3H), 2.32 (s, 3H), 3.03 (m, 2H), 6.67 (d, J=8 Hz, 1H), 6.87 (br. t, 1H, exchangeable), 6.99 (t, J=8 Hz, 1H), 7.79 (d. J=8 Hz, 1H), 9.46 (br. s, 1H, exchangeable).

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe organic fraction was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-10f101ec2f6c4b5493171f2687cac24d
Source dataset
uspto-grants-1999_11
Patent number
US05985872

Reaction notes

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