Acetic Acid → HCID 178518377, compound

HRID 351403Notes

Reaction equation

HRID 351403 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C[C:13](O)=[O:14].[O-]C#N.[Na+].[OH-].[Na+]>O>[Cl:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:13]([OH:14])[N:6]=[C:4]2[OH:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 788762-Amino-5-chlorobenzamideHCID 517096Sodium Cyanate

Product 1

HCID 178518377HCID 178518377, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

2-Amino-5-chlorobenzamide (Avocado) (3.00 g, 17.5 mmol, 1.0 eq.) was suspended in 105 mL of H2O and 1.75 mL of HOAc at rt. A 12 mL solution of H20 and sodium cyanate (2.80 g, 43.0 mmol, 2.46 eq.) was then added slowly. Stirred at 35° C. for 1 hour. Added 31.26 mL of 1.0 N NaOH slowly. Solids precipitated. Cooled to 0C. Carefully added conc. HCl to pH=3. Filtered solids. Solids were then stirred in diethyl ether then refiltered and pumped under high vacuum to give 3.36 grams of tan solids as product. LCMS detects (M+H)+=197.

Workup

  1. customat rt
  2. customSolids precipitated
  3. temperatureCooled to 0C
  4. filtrationFiltered solids
  5. stirringSolids were then stirred in diethyl ether

Sources & evidence

ORD record
ord-1253fc15704945b4a9866d6d8142edd7
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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