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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 745311
Notes
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Reaction equation

HRID 745311 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6212
Chloroform
Solvent
2×

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-3f89f339a61c447e9546bcd50eda7be4
Source dataset
uspto-grants-1986_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04598148

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes