Hydrochloric Acid → HCID 13723405, compound

HRID 1732114Notes

Reaction equation

HRID 1732114 reaction equation
C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[NH:16]([C:23]1[O:24][CH2:25][C:26](=O)[C:27]=1[C:28]([OH:30])=[O:29])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.[NH2:39][C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1.Cl>C(Cl)Cl>[C:17]1([NH:16][C:23]([C:27]2[C:28](=[O:30])[O:29][CH2:25][C:26]=2[NH:39][C:40]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7813p-ToluidineHCID 8471Triethylamine2×HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 69191962-Anilino-4-oxo-4,5-dihydrofuran-3-carboxylic acid

Product 1

HCID 13723405HCID 13723405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen atmosphere, BOP-Cl (5.09 grams, 0.02 mol) was added in one portion to a well-stirred solution of 2-anilino-4-oxo-3-furoic acid (4.38 grams, 0.02 mol) and triethylamine (2.8 ml, 20 mmol) in 34 ml methylene chloride, at 0° C. The reaction mixture was stirred at 0° C. for 45 min after which time 2.35 grams (0.022 mol) of p-toluidine in 17 ml methylene chloride were added over a period of 15 min. followed by the dropwise addition of triethylamine (2.8 ml, 20 mmol). The reaction mixture was stirred at 5°-10° C. for 30 min and at room temperature for 2 hours, poured into ice-water, acidified with 2N hydrochloric acid (pH 1), and then extracted with methylene chloride. The organic extract was washed with 5% aqueous sodium bicarbonate solution, dried over sodium sulfate, and the solvent evaporated under reduced pressure leaving the crude product which was recrystallized from ethanol. Yield: 3.37 grams, mp 181°-183° C. (R=C6H4CH3 --p).

Workup

  1. additionwere added over a period of 15 min.
  2. extractionextracted with methylene chloride
  3. extractionThe organic extract
  4. washwas washed with 5% aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-0550d3e4cc024fa9bc41fe3f53d0304e
Source dataset
uspto-grants-1986_11
Patent number
US04625040

Reaction notes

Loading…