Hydrochloric Acid → HCID 59139173, compound

HRID 599847Notes

Reaction equation

HRID 599847 reaction equation
[F:1][C:2]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1[C:6](=[O:22])[O:7][C:8]2[CH:15]=[C:14]([O:16][C:17](=[O:21])[N:18]([CH3:20])[CH3:19])[CH:13]=[CH:12][C:9]=2[C:10]=1[CH3:11].[Br:30]N1C(=O)CCC1=O.Cl>C1COCC1>[Br:30][CH2:11][C:10]1[C:9]2[CH:12]=[CH:13][C:14]([O:16][C:17](=[O:21])[N:18]([CH3:19])[CH3:20])=[CH:15][C:8]=2[O:7][C:6](=[O:22])[C:5]=1[CH2:4][C:3]1[CH:23]=[CH:24][CH:25]=[C:26]([N+:27]([O-:29])=[O:28])[C:2]=1[F:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 59139219HCID 59139219, compound

Product 1

HCID 59139173HCID 59139173, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

THF (0.9 mL) was added to dimethylcarbamic acid 3-(2-fluoro-3-nitrobenzyl)-4-methyl-2-oxo-2H-1-benzopyran-7-yl ester (compound 1g-1-4) (47.6 mg), and the resultant suspension was stirred at −78° C. for 20 minutes to yield a dark brown solution. This solution was added at 0° C. to a solution of N-bromosuccinimide (28 mg) in THF (0.8 mL) (which had been prepared in advance in a separate container), and the mixture was stirred at 0° C. for 40 minutes. This reaction solution was poured into 1N hydrochloric acid (0.119 mL) diluted with ice water (20 mL), and then extracted with ethyl acetate. The 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 (24.3 mg).

Workup

  1. customto yield a dark brown solution
  2. customhad been prepared in advance in a separate container), and the mixture
  3. extractionextracted with ethyl acetate
  4. extractionThe 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-74bd7dd656e140128c7dcc60f0c85a51
Source dataset
uspto-grants-2011_03
Patent number
US07897792B2

Reaction notes

Loading…