Acetone → HCID 19417509, compound

HRID 864965Notes

Reaction equation

HRID 864965 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[C:12]([NH:14][C:15]([NH2:17])=[NH:16])#[N:13].[CH3:18][C:19]([CH3:21])=O>>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([N:6]2[C:19]([CH3:21])([CH3:18])[N:16]=[C:15]([NH2:17])[N:14]=[C:12]2[NH2:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 3

HCID 180AcetoneHCID 122278893-Chloro-4-methoxyaniline--hydrogen chloride (1/1)HCID 178418324HCID 178418324, compound

Product 1

HCID 19417509HCID 19417509, compound

Procedure

A stirred mixture of 3.0 grams (0.019 mole) of 90% pure 3-chloro-4-methoxyaniline and 4 mL of concentrated hydrochloric acid in 20 mL of toluene was heated to reflux using a heat gun. The reaction mixture was then concentrated under reduced pressure to a residue. The residue was triturated with 50 mL of diethyl ether, and the resultant solid was collected by filtration. The solid was dried under vacuum, yielding 3.4 grams (0.018 mole) of 3-chloro-4-methoxyaniline hydrochloride. A stirred mixture of the aniline hydrochloride and 1.8 grams (0.022 mole) of cyanoguanidine in 25 mL of acetone was then heated at reflux for about 20 hours. The mixture was cooled, and a solid was collected by filtration. The solid was dried under vacuum, yielding 4.9 grams of 1-(3-chloro-4-methoxyphenyl)-2,4-diamino-6,6-dimethyl-1,6-dihydro-1,3,5-triazine hydrochloride, mp 232 ° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas then heated
  2. temperatureat reflux for about 20 hours
  3. temperatureThe mixture was cooled
  4. filtrationa solid was collected by filtration
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-4de5d58509204282b1b09c6e4b06bc5e
Source dataset
uspto-grants-1996_10
Patent number
US05565451

Reaction notes

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