Ethanol → HCID 86734365, compound

HRID 1414526Notes

Reaction equation

HRID 1414526 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:19][CH2:20]Cl)([CH2:16][CH2:17]Cl)[C:4]=2[CH:3]=1.[CH3:22][NH2:23].[CH2:24]([OH:26])C.[C:27](=[O:30])([OH:29])[O-].[Na+].[OH2:32]>>[OH2:26].[C:24]([OH:26])(=[O:32])[C:27]([OH:29])=[O:30].[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6]([C:5]4([CH2:19][CH2:20][N:23]([CH3:22])[CH2:17][CH2:16]4)[C:4]=2[CH:3]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 21487827HCID 21487827, compound

Product 1

HCID 86734365HCID 86734365, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-9,9-bis(2'-chloroethyl)-thioxanthene (0.9 g.), aqueous methylamine (10 ml.; 40% w/v.) and ethanol (15 ml.) is heated at 150° C. for 17 hours in a sealed tube. The cooled reaction mixture is diluted with water (50 ml.), basified with sodium bicarbonate solution and extracted with chloroform. The chloroform extract is dried (MgSO4), filtered, and evaporated. The residual gum (0.5 g.) is chromatographed on silica gel using ethanol/ethyl acetate (2:1) eluant. The product obtained after evaporation of the solvent is dissolved in ether, treated with an ethereal solution of oxalic acid, and the precipitated oxalate is dried at 80° C. in vacuo when there is obtained 2-chloro-1'-methylthioxanthene-9-spiro-4'-piperidine oxalate monohydrate (0.45 g.), m.p. 152°-155° C. (decomposition).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with chloroform
  3. extractionThe chloroform extract
  4. dry with materialis dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual gum (0.5 g.) is chromatographed on silica gel
  8. customThe product obtained
  9. customafter evaporation of the solvent
  10. dissolutionis dissolved in ether
  11. additiontreated with an ethereal solution of oxalic acid
  12. dry with materialthe precipitated oxalate is dried at 80° C. in vacuo when there

Sources & evidence

ORD record
ord-2e54de85f7064c13bd1400ee84c3bffb
Source dataset
uspto-grants-1977_01
Patent number
US04001418

Reaction notes

Loading…