Hydrochloric Acid → HCID 72486482, compound

HRID 2353920Notes

Reaction equation

HRID 2353920 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].S(O)(O)(=O)=O.[NH2:20][OH:21].[F:22][C:23]1[CH:24]=[C:25]([NH2:30])[CH:26]=[CH:27][C:28]=1[CH3:29].Cl>O>[F:22][C:23]1[CH:24]=[C:25]([NH:30][C:3](=[O:5])[CH:2]=[N:20][OH:21])[CH:26]=[CH:27][C:28]=1[CH3:29]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 99573-Fluoro-4-methylanilineHCID 24436Sodium SulfateHCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 72486482HCID 72486482, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of chloral hydrate (2.97 g, 17.98 mmol) and anhydrous sodium sulfate (15.20 g, 107 mmol) in water (50 mL) add a mixture of hydroxylamine sulfate (13.67 g, 83.23 mmol), 3-Fluoro-4-methyl-phenylamine (2 g, 15.98 mmol), concentrated hydrochloric acid (1.67 mL) in water (17 mL). Heat the mixture at 45° C. for 2 h and at 75° C. for 1 hr. Cool the mixture to room temperature and filter the solid. Wash the solid with water and ethyl ether. Dry the solid under vacuum to yield the title compound (2.96 g, 94%). 1H NMR (DMSO-d6, 300 MHz) δ 2.08 (d, J=1.0 Hz, 3H), 7.12 (t, J=8.8 Hz, 1H), 7.25 (dd, J=2.1, 8.2 Hz, 1H), 7.36 (dd, J=1.6, 12.4 Hz, 1H), 10.18 (s, 1H), 12.11 (s, 1H). MS (ES−): 195 (M−H).

Workup

  1. temperatureCool the mixture to room temperature
  2. filtrationfilter the solid
  3. washWash the solid with water and ethyl ether
  4. customDry the solid under vacuum

Sources & evidence

ORD record
ord-511721a1eeab493b99a052e43804a793
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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