1,2-Dichloroethane → HCID 54034496, compound

HRID 850626Notes

Reaction equation

HRID 850626 reaction equation
C(O[C:4](=[O:24])[CH2:5][N:6]([CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C.[OH-].[Na+].Cl.CN1CCOCC1.Cl.[CH3:36][NH:37][O:38][CH3:39].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(O)C.C(Cl)(Cl)Cl>[C:10]([O:9][C:7](=[O:8])[N:6]([CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=1)[CH2:5][C:4](=[O:24])[N:37]([O:38][CH3:39])[CH3:36])([CH3:11])([CH3:12])[CH3:13]

Participants

10

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 54283581HCID 54283581, compound

Product 1

HCID 54034496HCID 54034496, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 20-6 (23.4 g, 58.4 mmol) in ethanol (200 mL) was added NaOH (100 mL 1M solution in water, 100 mmol). After stirring for 1 h at 50° C., HCl (10.3 mL 12 M, 4.75 mmol) was added in 50 mL EtOH, and the mixture evaporated to give an oily residue. The residue was evaporated from ethanol three times, and then from acetonitrile three times, producing a yellow crusty solid which was dried under a vacuum of <2 mm Hg for 2 h. This residue was then slurried in acetonitrile (180 mL) and chloroform (180 mL), and NMM (41.7 mL, 379 mmol), N,O-dimethylhydroxylamine hydrochloride (11.9 g, 122 mmol), HOBT (10.2 g, 75.9 mmol), and EDC (14.5 g, 75.9 mmol) were added. After stirring for 15 h, the mixture was evaporated to dryness, the residue slurried in EtOAc, washed with sat. NaHCO3, brine, and dried over Na2SO4. Evaporative removal of the solvent followed by evaporation from toluene to remove the residual NMM gave 20-7 as a yellow oil.

Workup

  1. customthe mixture evaporated
  2. customto give an oily residue
  3. customThe residue was evaporated from ethanol three times
  4. customfrom acetonitrile three times, producing a yellow crusty solid which
  5. customwas dried under a vacuum of <2 mm Hg for 2 h
  6. stirringAfter stirring for 15 h
  7. customthe mixture was evaporated to dryness
  8. washwashed with sat. NaHCO3, brine
  9. dry with materialdried over Na2SO4
  10. customEvaporative removal of the solvent
  11. customfollowed by evaporation from toluene
  12. customto remove the residual NMM

Sources & evidence

ORD record
ord-db569064290b4db2ab020d3fc73014a6
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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