6-Amino-2-pyridinemethanol → HCID 54332416, compound

HRID 1902287Notes

Reaction equation

HRID 1902287 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][N:4]=[C:5]=[S:6].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[N:11]=1>C(#N)C>[F:1][C:2]([F:8])([F:7])[CH2:3][NH:4][C:5](=[S:6])[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][O:17][C:5](=[S:6])[NH:4][CH2:3][C:2]([F:8])([F:7])[F:1])[N:11]=1

Participants

4

Reactant 2

HCID 111826066-Amino-2-pyridinemethanolHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethane

Product 1

HCID 54332416HCID 54332416, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,2,2-Trifluoroethylisothiocyanate (2.82 g.) was added to a solution of 2-amino-6-hydroxymethylpyridine (2.1 g.) in acetonitrile (20 ml.) and the solution kept at room temperature for 18 hours and then evaporated to dryness. The residue was partitioned between ethyl acetate and water and the ethyl acetate phase separated, dried and evaporated to dryness. The residue was recrystallised from ethanol to give 2-[3-(2,2,2-trifluoroethyl)thioureido]-6-[N-(2,2,2-trifluoroethyl)-thiocarbamoyloxymethyl]pyridine (0.8 g.), m.p. 173°-175°.

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe ethyl acetate phase separated
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-2a6517a61399494e92c9b921b1a6f900
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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