Acetyl chloride → Acetamide, N-(6,7-dihydro-9,10-dimethoxy-4-oxo-4H-pyrimido(6,1-a)isoquinolin-2-yl)-N-(2,4,6-trimethylphenyl)-

HRID 1979726Notes

Reaction equation

HRID 1979726 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[C:16]1=[CH:22][C:23]([NH:27][C:28]3[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=3[CH3:36])=[N:24][C:25](=[O:26])[N:15]1[CH2:14][CH2:13]2.[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[C:16]1=[CH:22][C:23]([N:27]([C:37](=[O:39])[CH3:38])[C:28]3[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=3[CH3:36])=[N:24][C:25](=[O:26])[N:15]1[CH2:14][CH2:13]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18694579,10-dimethoxy-2-(2,4,6-trimethylanilino)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 3068155Acetamide, N-(6,7-dihydro-9,10-dimethoxy-4-oxo-4H-pyrimido(6,1-a)isoquinolin-2-yl)-N-(2,4,6-trimethylphenyl)-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1.2 ml of triethylamine are added first to an ice-cold solution of 9,10-dimethoxy-2-(2,4,6-trimethyl-anilino)-6,7-dihydro-4H-pyrimido(6,1-a)isoquinolin-4-one (1.6 g) in chloroform (40.0 ml), and then a solution of acetyl chloride (0.64 ml) in chloroform (10.0 ml) is added dropwise. The mixture is stirred for 2 hours. The chloroform solution is washed successively with water, sodium carbonate solution and water, and is then dried over anhydrous sodium sulfate. The solution is filtered and the filtrate evaporated to dryness in vacuo. The residue is triturated with diethyl ether to yield the desired compound in solid form. Yield 1.6 g, m.p. 210°-212° C. (dichloromethane-petroleum ether b.p. 60°-80° C.).

Workup

  1. washThe chloroform solution is washed successively with water, sodium carbonate solution and water
  2. dry with materialis then dried over anhydrous sodium sulfate
  3. filtrationThe solution is filtered
  4. customthe filtrate evaporated to dryness in vacuo
  5. customThe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-2f51aa8c8d9d4d24876eab048bcb89b3
Source dataset
uspto-grants-1984_11
Patent number
US04482556

Reaction notes

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