Hydrochloric Acid → HCID 59139149, compound

HRID 1046802Notes

Reaction equation

HRID 1046802 reaction equation
Br[CH2:2][C:3]1[C:8]2[CH:9]=[CH:10][C:11]([O:13][C:14](=[O:18])[N:15]([CH3:17])[CH3:16])=[CH:12][C:7]=2[O:6][C:5](=[O:19])[C:4]=1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[C:22]=1[F:30].[F-:31].[K+].C1OCCOCCOCCOCCOCCOC1.Cl>C(#N)C>[F:31][CH2:2][C:3]1[C:8]2[CH:9]=[CH:10][C:11]([O:13][C:14](=[O:18])[N:15]([CH3:17])[CH3:16])=[CH:12][C:7]=2[O:6][C:5](=[O:19])[C:4]=1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[C:22]=1[F:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2855718-Crown-62×HCID 522689Potassium Fluoride2×HCID 59139173HCID 59139173, compound

Product 1

HCID 59139149HCID 59139149, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (1.0 mL) was added to dimethylcarbamic acid 4-bromomethyl-3-(2-fluoro-3-nitrobenzyl)-2-oxo-2H-1-benzopyran-7-yl ester (compound 6b-1-4) (24.0 mg), and potassium fluoride (3.1 mg) and 18-crown-6 (13.2 mg) were added to the resultant suspension while stirring at room temperature. The mixture was stirred at 60° C. for 4 hours, potassium fluoride (3.1 mg) and 18-crown-6 (13.2 mg) were then added to the reaction solution, and the mixture was further stirred at 60° C. for 1.5 hours. This reaction solution was poured into 1N hydrochloric acid (0.110 mL) diluted with ice water (20 mL), and then extracted with ethyl acetate. The resultant organic layer extraction liquid was washed with saturated saline, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the resultant residue was purified by thin layer silica gel chromatography (hexane:ethyl acetate=1:1) to yield the title compound (14.7 mg).

Workup

  1. stirringThe mixture was stirred at 60° C. for 4 hours
  2. stirringthe mixture was further stirred at 60° C. for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. extractionThe resultant organic layer extraction liquid
  5. washwas washed with saturated saline
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled away under reduced pressure
  8. customthe resultant residue was purified by thin layer silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a1a1634ed76946b296a46cffe47f92f1
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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