Hydrochloric Acid → HCID 57167397, compound

HRID 1723013Notes

Reaction equation

HRID 1723013 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[Na].[CH2:8]1[O:27][C:11]([CH:15]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17][C:16]2=[O:26])(OCC)[O:10][CH2:9]1.Cl>CO.C(OCC)(=O)C>[CH2:8]1[O:27][C:11]([CH:15]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17][C:16]2=[O:26])([NH:2][OH:3])[O:10][CH2:9]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 86743317HCID 86743317, compound

Product 1

HCID 57167397HCID 57167397, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of hydroxylamine hydrochloride (11.6 g; 0.17 mol) in methanol (80 mL) was added at 40° C. and with stirring a solution of sodium methoxide in methanol (80 mL) prepared from 7.7 g (0.33 mol) of sodium. To this solution was added at 0° C. a solution of crude (V) (31.6 g; ca. 0.11 mol) in methanol (40 mL). This mixture was left at 25° C. with stirring for 24 h, and after cooling to 0° C. and with continued stirring, pH of the solution was adjusted to ca. 3 by addition of a solution of hydrogen chloride in ethyl acetate (2.5 M). The filtered and evaporated reaction mixture was extracted with ethyl acetate, and after filtration and addition of light petroleum (50 mL) compound (IV) crystallized. The yield of (IV) was 12.0 g (39%), M.p. 152.0-154.0° C. Anal. C11H18N2O6.

Workup

  1. waitThis mixture was left at 25° C.
  2. filtrationThe filtered
  3. customevaporated
  4. customreaction mixture
  5. extractionwas extracted with ethyl acetate
  6. filtrationafter filtration and addition of light petroleum (50 mL) compound (IV)
  7. customcrystallized

Sources & evidence

ORD record
ord-379991a16a0640d29d895b24a1dd9908
Source dataset
uspto-grants-1989_08
Patent number
US04859666

Reaction notes

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