Ethanol → HCID 57855962, compound

HRID 2039619Notes

Reaction equation

HRID 2039619 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8](N)[C:7](NC)=[C:6]([Cl:13])[C:5]=1[NH2:14].Cl.[C:17]([NH2:20])(=[NH:19])[CH3:18].[CH3:21]CO>>[CH3:1][O:2][C:3]([C:4]1[C:5]([NH2:14])=[C:6]([Cl:13])[C:7]2[N:19]([CH3:21])[C:17]([CH3:18])=[N:20][C:8]=2[CH:9]=1)=[O:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 67170Acetamidine monohydrochlorideHCID 57855886HCID 57855886, compound

Product 1

HCID 57855962HCID 57855962, compoundYield 58%

Conditions

Temperature
80 °C

Procedure

To a suspension of 1 g (3.48 mmol) of 2,5-diamino-3-chloro-4-methylamino-benzoic acid methyl ester (synthesis described in example H7) in 153 mL of EtOH is added 680 mg (6.97 mmol) of acetamidine hydrochloride. The mixture is stirred 2 days at a temperature of 80° C. Then, all the solvent is evaporated and the residue is suspended in EtOAc, the formed precipitate is filtrated and after evaporation the filtrate is purified by flash chromatography on silica gel and gave 510 mg (2.01 mmol, 58%) of a brown-reddish solid. LC/MS: 254/256 (M+1)+.

Workup

  1. customThen, all the solvent is evaporated
  2. filtrationthe formed precipitate is filtrated
  3. customafter evaporation the filtrate
  4. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b4b44f2025aa4106b945a2ec16f1ae06
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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