Triethylamine → HCID 14116583, compound

HRID 622650Notes

Reaction equation

HRID 622650 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]([CH2:57]CO)[CH2:48][CH2:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1.[Cl-].[Na+]>[CH2:40]([N:47]([CH2:57][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])[CH2:48][CH2:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 3830714HCID 3830714, compoundHCID 13960887HCID 13960887, compound

Product 1

HCID 14116583HCID 14116583, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-23 °C

Procedure

Trichloromethyl chloroformate (719 μl) was dissolved in 40 ml of tetrahydrofuran (THF). To the resulting solution, a mixture of 5-cyclopropylmethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyrimidine (1.65 g) and triethylamine (3.04 g) in THF (80 ml) was added under stirring at -23° C., followed by stirring for an additional one hour at -23° C. To the resulting mixture, 2-{N-benzyl-N-(3-phenylpropyl)amino}ethan-1-ol (6.73 g) in THF (40 ml) was added at 0° C., followed by stirring for 2 hour at room temperature. 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 evaporaed and the residue (ca. 12 g) was subjected to silica gel chromatography. By elution with a 1:1 mixture of ethyl acetate and n-hexane, the end compound was obtained in an amount of 2.14 g (yield: 69%).

Workup

  1. additionwas added
  2. stirringby stirring for an additional one hour at -23° C
  3. stirringby stirring for 2 hour at room temperature
  4. extractionsubjected to extraction with chloroform
  5. customAfter drying the extract
  6. washBy elution
  7. additionwith a 1:1 mixture of ethyl acetate and n-hexane
  8. customthe end compound was obtained in an amount of 2.14 g (yield: 69%)

Sources & evidence

ORD record
ord-7e43fce66e5841749532cc119095c0b0
Source dataset
uspto-grants-1988_09
Patent number
US04772602

Reaction notes

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