Sodium Carbonate → HCID 13503200, compound

HRID 256303Notes

Reaction equation

HRID 256303 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9][C:10]1[N:20]2[C:21]3[C:16]([CH2:17][CH2:18][CH2:19]2)=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=1.C(=O)([O-])[O-:23].[Na+].[Na+]>O>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9]([C:10]1[N:20]2[C:21]3[C:16]([CH2:17][CH2:18][CH2:19]2)=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=1)=[O:23]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 20163594HCID 20163594, compound

Product 1

HCID 13503200HCID 13503200, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-50 °C

Procedure

A solution of 5,6-dihydro-2-(2-pyridylmethylthio)-4H-imidazo-[4,5,1-ij]quinoline hydrochloride (4.0 g) in water (10 ml) was basified with sodium carbonate solution and extracted into chloroform. The extracts were dried (MgSO)4 and evaporated and the residue was dissolved in methylene chloride (50 ml) and cooled to -50° C. 3-chloroperoxybenzoic acid (2 g) was added with stirring and the solution was allowed to warm to -20° C. when a further (0.5 g) of 3-chloroperoxybenzoic acid was added and the solution was kept at 6° C. for 16 hours. It was then washed (Na2CO3 solution and brine), dried (MgSO4) and evaporated to give an oil which was purified by chromatography on alumina with ethyl acetate as eluent and crystallised from di-isopropylether to give the title compound as a quarterhydrate(2.1 g) mp 100°-102° C. (Found: C, 63.9; H, 5.1; N,14.0. C16H15N3OS, 1/4H2O requires C, 63.7; H,5.2; N,13.9%).

Workup

  1. extractionextracted into chloroform
  2. customevaporated
  3. dissolutionthe residue was dissolved in methylene chloride (50 ml)
  4. addition3-chloroperoxybenzoic acid (2 g) was added
  5. temperatureto warm to -20° C. when a further (0.5 g) of 3-chloroperoxybenzoic acid
  6. additionwas added
  7. washIt was then washed (Na2CO3 solution and brine)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give an oil which
  11. customwas purified by chromatography on alumina with ethyl acetate as eluent
  12. customcrystallised from di-isopropylether

Sources & evidence

ORD record
ord-ab4558b40edc426083d6abd253bd86eb
Source dataset
uspto-grants-1987_10
Patent number
US04703044

Reaction notes

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