Hydrochloric Acid → HCID 13723404, compound

HRID 1732113Notes

Reaction equation

HRID 1732113 reaction equation
[NH:1]([C:8]1[O:9][CH2:10][C:11](=O)[C:12]=1[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[Cl:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1.Cl>C(Cl)Cl.O.C(N(CC)CC)C>[C:2]1([NH:1][C:8]([C:12]2[C:13](=[O:15])[O:14][CH2:10][C:11]=2[NH:37][C:36]2[CH:38]=[CH:39][C:33]([Cl:32])=[CH:34][CH:35]=2)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 69191962-Anilino-4-oxo-4,5-dihydrofuran-3-carboxylic acid

Product 1

HCID 13723404HCID 13723404, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent2×

Procedure

Under nitrogen atmosphere, 8.5 ml of triethylamine was added dropwise over a period of 40 min to a solution of 2-anilino-4-oxo-3-furoic acid (13.37 grams, 0.061 mol) in 110 ml methylene chloride at 0° C. Then BOP-Cl was added in one portion and the mixture was stirred at 0°-5° C. for 45 min. A solution of p-chloroaniline (7.8 grams, 61 mmol) in 50 ml methylene chloride was added rapidly over 10 min followed by the dropwise addition (1.5 hours) of a solution of triethylamine (8.5 ml) in 10 ml methylene chloride. The reaction mixture was stirred at 0°-5° C. for 30 min and at room temperature for 20 hours. After cooling, 150 ml of water were added and the reaction mixture was acidified with 4N hydrochloric acid (pH 1), and then extracted with methylene chloride. The organic extract was washed sequentially with water, 5% aqueous solution of sodium bicarbonate, and water. The washed extract was dried over sodium sulfate and the solvent evaporated under reduced pressure. The crude product was recrystallized from toluene. Yield: 9.2 gram, mp 209°-210° C. (R=C6H4Cl--p).

Workup

  1. stirringThe reaction mixture was stirred at 0°-5° C. for 30 min and at room temperature for 20 hours
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. washwas washed sequentially with water, 5% aqueous solution of sodium bicarbonate, and water
  6. extractionThe washed extract
  7. dry with materialwas dried over sodium sulfate
  8. customthe solvent evaporated under reduced pressure
  9. customThe crude product was recrystallized from toluene

Sources & evidence

ORD record
ord-e18719d2d9964e0ca7162bc15ea5219b
Source dataset
uspto-grants-1986_11
Patent number
US04625040

Reaction notes

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