Methanol → N-(5-(methoxymethyl)pyridin-2-yl)-5-thiocyanatothiazol-2-amine

HRID 1685346Notes

Reaction equation

HRID 1685346 reaction equation
[S:1]([C:4]1[S:8][C:7]([NH:9][C:10]2[N:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=2)=[N:6][CH:5]=1)[C:2]#[N:3].[CH3:18]O>O=P(Cl)(Cl)Cl>[CH3:18][O:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:7]2[S:8][C:4]([S:1][C:2]#[N:3])=[CH:5][N:6]=2)=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 59200341HCID 59200341, compound

Product 1

HCID 59200492N-(5-(methoxymethyl)pyridin-2-yl)-5-thiocyanatothiazol-2-amine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
85 °C

Procedure

(6-(5-Thiocyanatothiazol-2-ylamino)pyridin-3-yl)methanol (0.094 g, 0.356 mmol) was dissolved in POCl3 (3 mL) and the reaction was heated at 85° C. for 3 hours. POCl3 was then evaporated and the resulting oil was washed with water to give a gummy solid. Methanol (10 mL) was added to the solid and the resulting suspension was stirred at 23° C. for over a month. Methanol was evaporated to almost dryness and water was added to precipitate the oil. The resulting solid was filtered and dried under vacuum to give the crude title material (0.109 g, quant.) which was used as such in the next reaction. HPLC ret. time (Condition A): 1.603 min. LC/MS (M+H)+: 279.

Workup

  1. customPOCl3 was then evaporated
  2. washthe resulting oil was washed with water
  3. customto give a gummy solid
  4. customMethanol was evaporated to almost dryness and water
  5. additionwas added
  6. customto precipitate the oil
  7. filtrationThe resulting solid was filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-f344b13b91de4f64ac8cf47837cca926
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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