1,2-Dichloroethane → HCID 15521926, compound

HRID 322083Notes

Reaction equation

HRID 322083 reaction equation
C(OC(=O)[CH:5]([N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][NH:14][C:13]=2[N:12]=1)[CH3:6])C.[OH-].[Na+].Cl.C[N:33]1[CH2:38]COC[CH2:34]1.Cl.CN[O:42][CH3:43].C1C=CC2N([OH:53])N=NC=2C=1.C(Cl)CCl>C(O)C.C(#N)C>[C:24]([O:23][C:21](=[O:22])[N:7]([CH2:5][CH2:6][C:38](=[O:53])[N:33]([O:42][CH3:43])[CH3:34])[CH2:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][NH:14][C:13]=2[N:12]=1)([CH3:25])([CH3:26])[CH3:27]

Participants

10

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 69710510HCID 69710510, compound

Product 1

HCID 15521926HCID 15521926, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-8 (5.6 g, 12.8 mmol) in ethanol (50 mL) was added NaOH (15 mL 1M solution in water, 15 mmol). After stirring for 1 h, HCl (15 mL 1M solution in water, 15 mmol) was added, 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 chloroform (5 mL) and acetonitrile (50 mL), and NMM (8.5 mL), N,O-dimethylhydroxylamine hydrochloride (2.5 g, 26 mmol), HOBT (1.7 g, 13 mmol) and EDC (2.4 g, 13 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 gave 4-9 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

Sources & evidence

ORD record
ord-f5f1de93df4949fc88dd1c76af276a0b
Source dataset
uspto-grants-2001_04
Patent number
US06211191B1

Reaction notes

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