Formaldehyde → HCID 10920614, compound

HRID 542571Notes

Reaction equation

HRID 542571 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[CH2:7]=[O:8].C(N(CC)CC)C.[CH3:16][OH:17]>C(O)(C)C>[CH3:1][C:2]1[NH:3][C:4]([CH2:16][OH:17])=[C:5]([CH2:7][OH:8])[N:6]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 8471TriethylamineHCID 127492-Methylimidazole

Product 1

HCID 10920614HCID 10920614, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
78 °C

Procedure

82 g (1 mole) of 2-methylimidazole and 220 g (2.2 moles) of 30% strength by weight aqueous formaldehyde solution are stirred for 1 hour at 60° C., 50.4 g (0.49 mole) of triethylamine are added to the mixture, and stirring is continued for 48 hours under reflux at about 78° C. The solution is evaporated to dryness under reduced pressure at a bath temperature of 60° C., 160 g of crude product being obtained during this procedure. The crude product is stirred with 128 g of methanol and 32 g of isopropanol, for 30 minutes in each case, at 50° C. and at 10° C. with cooling. The colorless solid is then filtered off, washed with twice 200 ml of acetone and dried for 12 minutes at 45° C. to give 91.6 g of 2-methyl-4,5-dihydroxymethylimidazole of melting point 182°-182.5° C. This corresponds to a yield of 64.5%. The purity (HPLC) is 99.8%.

Workup

  1. customThe solution is evaporated to dryness under reduced pressure at a bath temperature of 60° C., 160 g of crude product
  2. custombeing obtained during this procedure
  3. temperaturewith cooling
  4. filtrationThe colorless solid is then filtered off
  5. washwashed with twice 200 ml of acetone
  6. customdried for 12 minutes at 45° C.

Sources & evidence

ORD record
ord-dd305ee548004091bd06d99d8a7b50ce
Source dataset
uspto-grants-1987_04
Patent number
US04658035

Reaction notes

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