Formaldehyde → 1-Hydroxymethyl-2-(4-methoxy-2-picolylmercapto)1H-thieno[3,4-d]imidazole

HRID 231165Notes

Reaction equation

HRID 231165 reaction equation
[CH2:1]=[O:2].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][C:13]2[NH:17][C:16]3=[CH:18][S:19][CH:20]=[C:15]3[N:14]=2)[CH:6]=1>C(#N)C>[OH:2][CH2:1][N:14]1[C:15]2=[CH:20][S:19][CH:18]=[C:16]2[N:17]=[C:13]1[S:12][CH2:11][C:7]1[CH:6]=[C:5]([O:4][CH3:3])[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 139233692-(4-Methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole

Product 1

HCID 141543311-Hydroxymethyl-2-(4-methoxy-2-picolylmercapto)1H-thieno[3,4-d]imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
70 °C

Procedure

Under a nitrogen atmosphere, 0.7 ml of 37% strength aqueous formaldehyde solution in 3 ml of acetonitrile was added dropwise to 1.6 g (5.8 mmol) of 2-(4methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole dissolved in 50 of acetonitrile. The mixture was then stirred at 70° C. for 15 minutes. The solution was concentrated in vacuo, washed with water and saturated aqueous NaCl solution and dried over MgSO4. The residue obtained after evaporation resulted, after treatment with diisopropyl ether, in a semicrystalline crude product which crystallized from ethyl acetate. Melting point 125°-127° C.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washwashed with water and saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. customThe residue obtained
  5. customafter evaporation
  6. customresulted
  7. customafter treatment with diisopropyl ether, in a semicrystalline crude product which crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e8a97c58deb84714a2660c75b59b8fc9
Source dataset
uspto-grants-1989_07
Patent number
US04845118

Reaction notes

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