3-(2-Chloroethyl)-1,3-oxazolidin-2-one → HCID 131714810, compound

HRID 364190Notes

Reaction equation

HRID 364190 reaction equation
Cl.C([O:5][CH2:6][CH2:7][N:8]([CH2:12][CH2:13][N:14]1[C:22]2[CH:21]=[CH:20][C:19]([NH2:23])=[C:18]3[S:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:16]([C:17]=23)=[N:15]1)C(=O)C)(=O)C.[Cl:31][CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][O:36]C1=O>C(Cl)Cl.CO>[ClH:31].[OH:36][CH2:37][CH2:38][NH:34][CH2:33][CH2:32][NH:23][C:19]1[CH:20]=[CH:21][C:22]2[N:14]([CH2:13][CH2:12][NH:8][CH2:7][CH2:6][OH:5])[N:15]=[C:16]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[S:24][C:18]=1[C:17]=23

Participants

4

Reactant 2

HCID 756333-(2-Chloroethyl)-1,3-oxazolidin-2-oneHCID 49860271HCID 49860271, compound

Product 1

HCID 131714810HCID 131714810, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5.1 g (0.012 mol) of N-[2-(acetyloxy)ethyl]-N-[2-(5-amino-2H[1]benzothiopyrano[4,3,2-cd]indazol-2-yl)ethyl]acetamide, hydrochloride salt and 11.6 g (0.077 mol) of 3-(β-chloroethyl)-2-oxazolidinone was stirred at 150° C. for 2 hours, dissolved in 20 ml of a CH2Cl2 /MeOH (20/1) mixture, and flash chromatographed over silica gel, eluting with a CH2Cl2 /MeOH (20/1) mixture. The appropriate fractions were combined and concentrated to dryness in vacuo. The residue was treated with 20 ml of 2N KOH in MeOH, 10 ml of H2O, and 10 ml of THF, and the mixture was heated under reflux under a N2 atmosphere for 16 hours. The mixture was treated with 100 ml of H2O and 100 ml of CH2Cl2 and the layers were separated. The aqueous phase was extracted twice with CH2Cl2 and the Ch2Cl2 extracts were combined, dried (MgSO4), and concentrated to dryness in vacuo. The residue was dissolved in 50 ml of EtOH and treated with an excess of i-PrOH saturated with gaseous HCl. The precipitate was collected and recrystallized from MeOH to give 6.0 g of product, mp 222°-225° C.

Workup

  1. customchromatographed over silica gel
  2. washeluting with a CH2Cl2 /MeOH (20/1) mixture
  3. concentrationconcentrated to dryness in vacuo
  4. additionThe residue was treated with 20 ml of 2N KOH in MeOH, 10 ml of H2O, and 10 ml of THF
  5. temperaturethe mixture was heated
  6. temperatureunder reflux under a N2 atmosphere for 16 hours
  7. additionThe mixture was treated with 100 ml of H2O and 100 ml of CH2Cl2
  8. customthe layers were separated
  9. extractionThe aqueous phase was extracted twice with CH2Cl2
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated to dryness in vacuo
  12. dissolutionThe residue was dissolved in 50 ml of EtOH
  13. additiontreated with an excess of i-PrOH saturated with gaseous HCl
  14. customThe precipitate was collected
  15. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-9ac7595094c5423cb5fd8133706aa4a1
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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