Triethylamine → HCID 14368129, compound

HRID 622649Notes

Reaction equation

HRID 622649 reaction equation
Cl[C:2]([O:4][C:5](Cl)(Cl)Cl)=[O:3].[CH:9]1([CH2:12][O:13][C:14]([C:16]2[CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N+:30]([O-:32])=[O:31])[N:18]=[C:19]([CH3:23])[NH:20][C:21]=2[CH3:22])=[O:15])[CH2:11][CH2:10]1.C(N(CC)CC)C.[CH2:40]([N:47]([CH2:49]CO)[CH3:48])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1.[Cl-].[Na+]>[CH2:40]([N:47]([CH2:49][CH2:5][O:4][C:2]([N:18]1[CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N+:30]([O-:32])=[O:31])[C:16]([C:14]([O:13][CH2:12][CH:9]2[CH2:11][CH2:10]2)=[O:15])=[C:21]([CH3:22])[N:20]=[C:19]1[CH3:23])=[O:3])[CH3:48])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 66876N-Benzyl-N-methylethanolamineHCID 13960887HCID 13960887, compound

Product 1

HCID 14368129HCID 14368129, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-23 °C

Procedure

Trichloromethyl chloroformate (144 μl) was dissolved in 10 ml of tetrahydrofuran (THF). To the resulting solution, a mixture of 5-cyclo-propylmethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyrimidine (329 mg) and triethylamine (607 ml) in THF (20 ml) was added under stirring at -23° C., followed by stirring for an additional one hour. To the resulting mixture, 2-(N-benzyl-N-methylamino)ethan-1-ol (991 mg) in THF (10 ml) was added at 0° C., followed by stirring for one hour. The stirring was continued for one more hour at room temperature and, thereafter, the reaction mixture was diluted with a saturated aqueous solution of sodium chloride and subjected to extraction with chloroform. After drying the extract, the solvent was evaporated and the residue (1.32 g) was subjected to silica gel chromatography. By elution with 1% methanol-chloroform, the desired compound was obtained in an amount of 354 mg (yield: 68%). The physicochemical data of the compound are shown in Table 1.

Workup

  1. additionwas added
  2. stirringby stirring for an additional one hour
  3. stirringby stirring for one hour
  4. customwas continued for one more hour at room temperature
  5. extractionsubjected to extraction with chloroform
  6. customAfter drying the extract
  7. customthe solvent was evaporated
  8. washBy elution with 1% methanol-chloroform

Sources & evidence

ORD record
ord-13417f1f8a88450c8ff43bb362a454df
Source dataset
uspto-grants-1988_09
Patent number
US04772602

Reaction notes

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