1,2-Dichloroethane → HCID 11761020, compound

HRID 850597Notes

Reaction equation

HRID 850597 reaction equation
C(O[C:4](=[O:27])[CH2:5][N:6]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:7][CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][CH2:15][CH2:14][NH:13][C:12]=2[N:11]=1)C.[OH-].[Na+].Cl.C(N(CC)CC)C.Cl.[CH3:39][NH:40][O:41][CH3:42].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(O)C.O>[C:23]([O:22][C:20](=[O:21])[N:6]([CH2:5][C:4](=[O:27])[N:40]([O:41][CH3:42])[CH3:39])[CH2:7][CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][CH2:15][CH2:14][NH:13][C:12]=2[N:11]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

10

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 11731596HCID 11731596, compound

Product 1

HCID 11761020HCID 11761020, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-8 (1.49 g, 3.96 mmol) in ethanol (8 mL) was added NaOH (4.36 mL 1M solution in water, 4.36 mmol). After stirring for 1 h at 50° C., HCl (4.75 mL of a 1M solution in water, 4.75 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 (15 mL), and triethylamine (2.75 mL, 19.8 mmol), N,O-dimethylhydroxylamine hydrochloride (0.772 g, 7.92 mmol), HOBT (1 g) and EDC (0.91 g, 4.75 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 2-9 as a yellow oil. TLC Rf =0.49 (silica, 70:25:5 chloroform /ethyl acetate /methanol) 1H NMR (300 MHz, CDCl3) δ 7.05 (m, 1H), 6.38 (m, 1H), 4.81 (br s, 1H), 3.69, m, 3H), 3.37 (m, 4H), 3.18 (s, 3H), 2.64 (m, 2H), 2.53 (m, 2H), 1.88 (m, 4H), 1.44 (m, 9H).

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-ed02e0217b3341f9b23cc6d47f5ecc07
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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