Ammonia → Ethyl 5-carbamoyl-2,4-dimethylfuran-3-carboxylate

HRID 553234Notes

Reaction equation

HRID 553234 reaction equation
Cl.C([N:4]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH3:24][C:25]1[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:28]([CH3:35])[O:27][C:26]=1[C:36]([OH:38])=O.N>O.N1C=CC=CC=1>[CH3:24][C:25]1[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:28]([CH3:35])[O:27][C:26]=1[C:36]([NH2:4])=[O:38]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57955825HCID 57955825, compound

Product 1

HCID 57955774Ethyl 5-carbamoyl-2,4-dimethylfuran-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (248 mg, 1.30 mmol) and 1-hydroxybenzotriazole monohydrate (199 mg, 1.30 mmol) were added to a pyridine (4 ml) solution of the 3,5-dimethyl-4-ethoxycarbonylfuran-2-carboxylic acid (250 mg, 1.18 mmol) obtained in Example 2 (1). After a 28% aqueous ammonia solution (0.19 ml, 11.8 mmol) was added, heated to 80° C. and stirred for 4 hours. The mixture was cooled to room temperature with stirring, and after addition of water to reaction mixture, precipitate was collected by filtration, thereby giving 3,5-dimethyl-4-ethoxycarbonylfuran-2-carboxamide (176 mg, 71%) as a white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringwith stirring
  3. customto reaction mixture, precipitate
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a68a6c49c0f843cb9fd92f1227728431
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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