2-Amino-4-methylthiazole → HCID 7997300, compound

HRID 635845Notes

Reaction equation

HRID 635845 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.CO[CH:10](OC)[N:11]([CH3:13])[CH3:12]>C1(C)C=CC=CC=1>[CH3:7][C:5]1[N:6]=[C:2]([N:1]=[CH:10][N:11]([CH3:13])[CH3:12])[S:3][CH:4]=1

Participants

4

Reactant 2

HCID 741432-Amino-4-methylthiazoleHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 7997300HCID 7997300, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution 2-amino-4-methylthiazole (Formula C-1)(11.4 g) in toluene (100 ml) at 25° was treated with dimethylformamide dimethyl acetal (15.9 mL, 200 mmol), dropwise over five minutes. The mixture was heated to reflux temperature for 22 hours. The reaction was cooled to 25° and the solvent evaporated to an orange oil (17 g). The oil was triturated with hexane to yield yellow crystals. Recrystallization from warm hexane gave N′-(4-Methyl-2-thiazolyl)-N,N-dimethyl-methanimidamide (Formula C-2) (16.9 g, 99.6%), m.p. 54-56°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature for 22 hours
  3. temperatureThe reaction was cooled to 25°
  4. customthe solvent evaporated to an orange oil (17 g)
  5. customThe oil was triturated with hexane
  6. customto yield yellow crystals
  7. customRecrystallization
  8. temperaturefrom warm hexane

Sources & evidence

ORD record
ord-d85c8beb82f14b2f8e727a26a3cac187
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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