Hydrochloric Acid → HCID 178517401, compound

HRID 908608Notes

Reaction equation

HRID 908608 reaction equation
N[C:2]1[S:3][C:4]2[C:9]([OH:10])=[N:8][C:7]([CH:11]3[CH2:13][CH2:12]3)=[N:6][C:5]=2[N:14]=1.N([O-])=O.[Na+].[ClH:19]>[OH-].[Na+]>[Cl:19][C:2]1[S:3][C:4]2[C:9]([OH:10])=[N:8][C:7]([CH:11]3[CH2:13][CH2:12]3)=[N:6][C:5]=2[N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 178508244HCID 178508244, compound

Product 1

HCID 178517401HCID 178517401, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

The compound (1.2 g) obtained in Step 3 was suspended in 2N aqueous sodium hydroxide solution (18 ml) and, under ice-cooling, sodium nitrite (1.2 g) was added in several portions. The obtained suspension was slowly added dropwise to a concentrated aqueous hydrochloric acid solution (18 ml) heated to 80° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by filtration, washed with water and dried to give the title compound (0.60 g). The filtrate was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtrated, and concentrated under reduced pressure to give a crude product (0.34 g) containing the title compound as a main component. The obtained crude crystals were suspended in a mixed solvent of hexane and ethyl acetate, collected by filtration and dried to give the title compound (0.26 g).

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-be1b86a3393b464f87fb9eb77634845c
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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