Triethylamine → N'-(4,5-Dimethyl-2-thiazolyl)-N,N-dimethyl-methanimidamide

HRID 635837Notes

Reaction equation

HRID 635837 reaction equation
Cl.[NH2:2][C:3]1[S:4][C:5]([CH3:9])=[C:6]([CH3:8])[N:7]=1.[CH2:10]([N:12]([CH2:15]C)[CH2:13]C)C.COC(OC)N(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:8][C:6]1[N:7]=[C:3]([N:2]=[CH:10][N:12]([CH3:15])[CH3:13])[S:4][C:5]=1[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 162113874,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1)

Product 1

HCID 54260345N'-(4,5-Dimethyl-2-thiazolyl)-N,N-dimethyl-methanimidamideYield 78.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-amino-4,5-dimethylthiazole hydrochloride (4.92 g, 30 mmol) (Formula A-1) in toluene (60 mL) was treated with triethylamine (4.5 mL, 35 mmol) and vigorously stirred for 30 minutes. The mixture was treated with dimethylformamide dimethyl acetal (7.3 mL, 60 mmol) and heated at reflux temperature for 2 hours. The solution was cooled, diluted with ethyl acetate, washed with saline, dried and evaporated. The residue was crystallized from hexane to provide pure N′-(4,5-Dimethyl-2-thiazolyl)-N,N-dimethyl-methanimidamide (Formula A-2) (4.31 g, 77%), m.p. 47-58°.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 hours
  3. temperatureThe solution was cooled
  4. washwashed with saline
  5. customdried
  6. customevaporated
  7. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-69ae5c2f0e624d4aab625b260fb1bdc1
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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