Nitric Acid → HCID 131729650, compound

HRID 1695261Notes

Reaction equation

HRID 1695261 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:28])[C:13]2[O:19][C:18]3[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:17]=3[CH2:16][S:15](=[O:26])(=[O:25])[C:14]=2[CH:27]=1)=[O:9].[N+:29]([O-])([OH:31])=[O:30]>>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:28])[C:13]2[O:19][C:18]3[C:20]([Cl:24])=[CH:21][C:22]([N+:29]([O-:31])=[O:30])=[CH:23][C:17]=3[CH2:16][S:15](=[O:25])(=[O:26])[C:14]=2[CH:27]=1)=[O:9]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 131728525HCID 131728525, compound

Product 1

HCID 131729650HCID 131729650, compound

Conditions

Temperature
5 °C

Procedure

Concentrated sulfuric acid (240 mL, 4.2 mol) was added to a solution of compound of Example 1i (37 g, 0.105 mol) in concentrated nitric acid (1100 mL, 17.34 mol) at 5° C. The reaction mixture was stirred at 5° C. for 25 min, and then at 40° C. for 4.5 h. Reaction mixture was quenched into ice water (2500 mL), the solid precipitated was filtered, washed with water till filtrate was neutral to pH and dried to obtain the title compound. Yield: 38 g (90.91%); 1H NMR (CDCl3, 300 MHz): δ 2.7 (s, 3H, CH3), 3.90 (s, 3H, OCH3), 4.79 (s, 2H, CH2), 8.10 (s, 1H, Ar), 8.22 (s, 1H, Ar), 8.38 (s, 1H, Ar), 8.48 (s, 1H, Ar); MS: m/e (ES−) 396 (M−1).

Workup

  1. waitat 40° C. for 4.5 h
  2. customReaction mixture
  3. customwas quenched into ice water (2500 mL)
  4. customthe solid precipitated
  5. filtrationwas filtered
  6. washwashed with water till filtrate
  7. customdried

Sources & evidence

ORD record
ord-ba1d3a17f3a645e4a61a61d04a065aa9
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

Loading…