Methanimidamide, hydrochloride (1:1) → HCID 135767899, compound

HRID 2405757Notes

Reaction equation

HRID 2405757 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([NH2:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[CH:16](N)=[NH:17]>>[Cl:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[N:11]=[CH:16][NH:17][C:7]2=[O:9]

Participants

3

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 214739642-Amino-5-chloro-4-nitrobenzoic acid

Product 1

HCID 135767899HCID 135767899, compoundYield 84.2%

Conditions

Temperature
205 °C

Procedure

A mixture of 5-chloro-4-nitroanthranilic acid (8.7 g, 0.040 mol) and formamidine hydrochloride (4.9 g, 60 mmol) were ground to a fine, intimate powder using a mortar and pestle. The mixture was transferred into a 250 mL round bottomed flask and immersed in an oil bath maintained at 205° C. After 40 min, LCMS analysis of the reaction mixture showed mass corresponding to the product. The reaction mixture was cooled and the crude product was crushed into pieces and washed several times with saturated NaHCO3 (300 mL) and water (200 mL). The solid was air dried and triturated with a minimum amount of MeOH (20 mL) to obtain 6-chloro-7-nitroquinazoline-4-one (7.6 g, 83%) as a tan powder.

Workup

  1. customThe mixture was transferred into a 250 mL round bottomed flask
  2. customimmersed in an oil bath
  3. temperatureThe reaction mixture was cooled
  4. washwashed several times with saturated NaHCO3 (300 mL) and water (200 mL)
  5. customdried
  6. customtriturated with a minimum amount of MeOH (20 mL)

Sources & evidence

ORD record
ord-9758a1b25dfe40a9a7b7402495333a4e
Source dataset
uspto-grants-2014_08
Patent number
US08809326B2

Reaction notes

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