Oxalic acid dihydrate → HCID 21481141, compound

HRID 435724Notes

Reaction equation

HRID 435724 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[C:9]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][O:21][C:20]4=[O:24])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[CH:3]=1.[BH4-].[Na+].O.O.C(O)(=O)C(O)=O>COCCOCCOC>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[CH:9]([N:11]3[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][O:21][C:20]4=[O:24])[CH2:15][CH2:16]3)[CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 61373Oxalic acid dihydrateHCID 4311764Sodium borohydrideHCID 214560453-[2-[4-(2-Chloro-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone

Product 1

HCID 21481141HCID 21481141, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Conditions

Temperature
100 °C

Procedure

750 mg of 3-[2-[4-(2-chloro-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone, 0.6 g of sodium borohydride and 30 ml of diglyme are treated dropwise under an argon atmosphere at 20°-30° C over a period of 15 minutes with 2.7 g of oxalic acid dihydrate in 15 ml of diglyme. The mixture is heated for 4 hours at an internal temperature of 100° C and subsequently evaporated under reduced pressure. The residue is treated with chloroform and 2-N sodium hydroxide solution. After equilibration, the aqueous phase is separated and washed twice with chloroform. The combined chloroform extracts are washed with water, dried over potassium carbonate and active carbon, filtered and evaporated under reduced pressure. There is obtained 3-[2-[4-(2-chloro-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone in the form of a brown oil. The maleate of melting point 173°-175° C is prepared by treatment with maleic acid in ethanol/ether.

Workup

  1. customsubsequently evaporated under reduced pressure
  2. additionThe residue is treated with chloroform and 2-N sodium hydroxide solution
  3. customAfter equilibration, the aqueous phase is separated
  4. washwashed twice with chloroform
  5. washThe combined chloroform extracts are washed with water
  6. dry with materialdried over potassium carbonate and active carbon
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2db3ff3144d143a19b85f40c0efbfb36
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

Loading…