Acetyl chloride → HCID 13712583, compound

HRID 1757945Notes

Reaction equation

HRID 1757945 reaction equation
[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]([CH2:16][OH:17])[C:7](=[O:18])[CH2:6][O:5]1)(=[O:3])[CH3:2].[O:19]1CC[CH2:21][CH2:20]1.C(Cl)(=O)C>C(N(CC)CC)C>[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]([CH2:16][O:17][C:20](=[O:19])[CH3:21])[C:7](=[O:18])[CH2:6][O:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 13712582HCID 13712582, compound

Product 1

HCID 13712583HCID 13712583, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.0 g. (4 mmoles) of 2-acetyl-3-phenyl-4-hydroxymethyl-tetrahydro-1,2,4-oxadiazin-5-one in 10 ml. of dry tetrahydrofurane 0.72 ml. of dry triethyl amine are added. The solution is cooled to 0° C. and 0.36 ml. (0.40 g., 5 mmoles) of acetyl chloride are added dropwise at this temperature. The mixture is stirred at room temperature for two hours, the precipitated triethyl amine hydrochloride is filtered off and the filtrate is evaporated to dryness. The residue is dissolved in 10 ml. of ethyl acetate, the solution is shaken with 3 ml. of a 1 N aqueous sodium hydrocarbonate solution, 3 ml. of a 1 N aqueous hydrochloric acid solution and finally with two 3-ml. portions of water, whereupon it is dried with anhydrous sodium sulfate and evaporated to dryness. The residue is recrystallized from a mixture of 3 ml. of diethyl ether and 6 ml. of n-hexane. 0.90 g. (77%) of 2-acetyl- 3-phenyl-4-acetoxymethyl-tetrahydro-1,2,4-oxadiazin-5-one are obtained, melting at 75° C. to 76° C. RfA =0.7.

Workup

  1. filtrationthe precipitated triethyl amine hydrochloride is filtered off
  2. customthe filtrate is evaporated to dryness
  3. dissolutionThe residue is dissolved in 10 ml
  4. stirringof ethyl acetate, the solution is shaken with 3 ml
  5. dry with materialportions of water, whereupon it is dried with anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue is recrystallized from a mixture of 3 ml

Sources & evidence

ORD record
ord-fd2efcabdd874d98b5a0c2d30203ee19
Source dataset
uspto-grants-1983_02
Patent number
US04371534

Reaction notes

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