Potassium Carbonate → HCID 11525330, compound

HRID 1713022

Reaction equation

HRID 1713022 reaction equation
C(O[C:4]([C:6]1[NH:10][C:9]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[O:13][C:8]=2[CH:7]=1)=[O:5])C.C(OC(=O)C(CC)CCN1C(=S)N2C3C=C(C4C=CC([N+]([O-])=O)=CC=4)OC=3C=C2C1=O)C.[CH2:55]([O:57][C:58](=[O:67])[CH2:59][C:60]([CH3:66])([CH3:65])[CH2:61][N:62]=[C:63]=[S:64])[CH3:56].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH2:55]([O:57][C:58](=[O:67])[CH2:59][C:60]([CH3:66])([CH3:65])[CH2:61][N:62]1[C:63](=[S:64])[N:10]2[C:9]3[CH:11]=[C:12]([C:14]4[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=4)[O:13][C:8]=3[CH:7]=[C:6]2[C:4]1=[O:5])[CH3:56]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 594634452-(4-nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl esterHCID 86618327HCID 86618327, compoundHCID 86618331Ethyl 4-isothiocyanato-3,3-dimethylbutanoate

Product 1

HCID 11525330HCID 11525330, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

2-(4-nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester (212 mg, 0.71 mmol, 1 molequivalent), prepared as described hereinabove (see, preparation of Compound 1), was placed in a round bottom flask and 4-isothiocyanato-3,3-dimethyl-butyric acid ethyl ester (1.4 grams, 7.1 mmol, 10 molequivalents) was added thereto, followed by addition of grinded anhydrous potassium carbonate (K2CO3; 147 mg, 1.1 mmol, 1.5 molequivalents). The mixture was heated while stirring at 140° C. for 16 hours. The reaction mixture was thereafter dissolved in chloroform and 5% citric acid solution, the organic phase was extracted, and the aqueous layer was washed with chloroform several times. The combined organic layers were dried over Na2SO4, the solvent was removed under reduced pressure, and the crude product was triturated in ethanol to give Compound 7 (322 mg, 40% yield) as an orange solid.

Workup

  1. customwas placed in a round bottom flask
  2. temperatureThe mixture was heated
  3. extraction5% citric acid solution, the organic phase was extracted
  4. washthe aqueous layer was washed with chloroform several times
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customthe crude product was triturated in ethanol

Sources & evidence

ORD record
ord-bce17004c4be48ebab39dcc0564a406c
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Linked notes

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