Formaldehyde → HCID 13712582, compound

HRID 1757944Notes

Reaction equation

HRID 1757944 reaction equation
[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:8][C:7](=[O:16])[CH2:6][O:5]1)(=[O:3])[CH3:2].[O:17]1CCC[CH2:18]1.C=O>C(N(CC)CC)C>[C:1]([N:4]1[CH:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:8]([CH2:18][OH:17])[C:7](=[O:16])[CH2:6][O:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 134224Rgh 4615

Product 1

HCID 13712582HCID 13712582, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 1.1 g. (5 mmoles) of 2-acetyl-3-phenyl-tetrahydro-1,2,4-oxadiazin-5-one in 10 ml. of tetrahydrofurane 1 ml. of triethyl amine and 0.4 ml. of a 37% aqueous formaldehyde solution are added. The mixture is allowed to stand at room temperature overnight and is then evaporated to dryness. The residue is triturated with diethyl ether and the product is isolated by filtration. 1.16 g. (93%) of 2-acetyl-3-phenyl-4-hydroxymethyl-tetrahydro-1,2,4-oxadiazin-5-one are obtained, melting at 123° to 126° C. RfA =0.5.

Workup

  1. customis then evaporated to dryness
  2. customThe residue is triturated with diethyl ether
  3. customthe product is isolated by filtration

Sources & evidence

ORD record
ord-81ce44e36bb343f9ac6c4348e7c2e693
Source dataset
uspto-grants-1983_02
Patent number
US04371534

Reaction notes

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