Hydrochloric Acid → 4-(Methoxymethyl)-1,3-thiazol-2-amine

HRID 252274Notes

Reaction equation

HRID 252274 reaction equation
Br[CH2:2][C:3]([CH2:5]Br)=O.[NH2:7][C:8]([NH2:10])=[S:9].Cl.[CH3:12][OH:13]>O>[CH3:12][O:13][CH2:2][C:3]1[N:7]=[C:8]([NH2:10])[S:9][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 699521,3-Dibromo-2-propanoneHCID 2723790Thiourea

Product 1

HCID 230925274-(Methoxymethyl)-1,3-thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Dibromoacetone (15 g, 52 mmol) and thiourea (4.05 g, 53.2 mmol, 1.02 equiv.) in methanol were refluxed overnight. The reaction mixture was diluted with water and the pH was adjusted to 1 with HCl 25%, followed by extraction with ethyl acetate. The pH of the aqueous layer was adjusted to 8-9 using solid sodium carbonate. The aqueous layer was extracted with ethyl acetate, and the combined organic extracts were washed with brine, dried over magnesiumsulfat dihydrate, filtered and evaporated. The crude product was purified on silica-gel (NH2-modified) with ethyl acetate/n-heptane as eluent yielding a white solid: 340 mg. MS (ES) m/e 145 (M+H)

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over magnesiumsulfat dihydrate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified on silica-gel (NH2-modified) with ethyl acetate/n-heptane as eluent
  8. customyielding a white solid

Sources & evidence

ORD record
ord-68b06c066e9c43f6a75255326bba087d
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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