Acetyl chloride → HCID 15508342, compound

HRID 1419507Notes

Reaction equation

HRID 1419507 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH:5]1[CH2:10][CH2:9][NH:8][CH:7]=[C:6]1[C:11]([O:13][CH3:14])=[O:12].O1CCCC1.C(N(CC)CC)C>C(OCC)(=O)C>[C:1]([N:5]1[CH2:10][CH2:9][NH:8][CH:7]=[C:6]1[C:11]([O:13][CH3:14])=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 15508341HCID 15508341, compound

Product 1

HCID 15508342HCID 15508342, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

15.10 g (192.5 mmol) of acetyl chloride was added dropwise over 25 minutes to 25.00 g (175.9 mmol) of methyl 1,4,5,6-tetrahydropyrazine-2-carboxylate, 250 ml of tetrahydrofuran and 21.30 g (210.5 mmol) of triethylamine at 0° C. The mixture was then heated to room temperature and, after 1 hour, 200 ml of ethyl acetate were added. The aqueous phase was washed a further 3 to 4 times with a total of 500 ml of ethyl acetate and the combined organic extracts were dried over magnesium sulfate. After the solvent had been stripped off, 22.30 g (69%) of the title compound were obtained as a yellow oil. Recrystallization from ethyl acetate gave methyl 1-acetyl-1,4,5,6-tetrahydropyrazine-2-carboxylate in the form of a light yellow, crystalline solid. The melting point of the title compound was: 136° to 139° C. Other data concerning the title compound was:

Workup

  1. washThe aqueous phase was washed a further 3 to 4 times with a total of 500 ml of ethyl acetate
  2. dry with materialthe combined organic extracts were dried over magnesium sulfate

Sources & evidence

ORD record
ord-2de0d2eeb4ce48d49a40ec2582c2cb87
Source dataset
uspto-grants-1999_03
Patent number
US05886181

Reaction notes

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