Hydrochloric Acid → HCID 178468865, compound

HRID 2099437Notes

Reaction equation

HRID 2099437 reaction equation
[N:1]#[C:2][NH2:3].[CH2:4]([O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10](N)[CH:9]=1)[CH3:5].Cl.[N+:18]([O-:21])([O-:20])=[O:19].[NH4+:22]>C(O)C.O>[N+:18]([O-:21])([OH:20])=[O:19].[CH2:4]([O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH:1][CH:2]=[N:3][NH2:22])[CH:9]=1)[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 22985Ammonium nitrateHCID 12607966Ethyl 3-amino-4-methylbenzoate

Product 1

HCID 178468865HCID 178468865, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

Cyanamide (Fluka, Buchs, Switzerland; 77.4 g, 1.842 mol) is added to a solution of 3-amino-4-methylbenzoic acid ethyl ester (J. Med. Chem. 16, 118-122, 1973; 150 g, 0.837 mol) in 850 mL of ethanol. Hydrochloric acid (Fluka, Buchs, Switzerland; 108 mL of 12M, 1.27 mol) is then added dropwise over 15 min and the reaction mixture is then stirred at 90° C. (bath temperature) for 15 hours. The solvent is evaporated off under reduced pressure to give a residue which is treated with water (1000 mL) and stirred with cooling at 5-10° C. A solution of ammonium nitrate (Merck, Darmstadt, Germany; 134.8 g, 1.68 mol) in water (400 mL) is added dropwise over 30 min. followed by ice-water (1200 mL). After stirring for an additional 30 min. the product is filtered off, washed with ice-water (3×1000 mL) and air-dried. The residue is washed with diethyl ether (2×2000 m L) and dried in vacuo at 500 to give the title compound as a crystalline solid, m.p. 195-197° C.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. customto give a residue which
  3. stirringstirred
  4. temperaturewith cooling at 5-10° C
  5. stirringAfter stirring for an additional 30 min. the product
  6. filtrationis filtered off
  7. washwashed with ice-water (3×1000 mL)
  8. customair-dried
  9. washThe residue is washed with diethyl ether (2×2000 m L)
  10. customdried in vacuo at 500

Sources & evidence

ORD record
ord-f2927d705c424f91b86e8252e106e3bc
Source dataset
uspto-grants-2009_08
Patent number
US07569566B2

Reaction notes

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