Sulfuric Acid → HCID 178418516, compound

HRID 4452Notes

Reaction equation

HRID 4452 reaction equation
[Na].Cl.[CH3:3][C@@H:4]([CH2:20][CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[NH:16])=[CH:13][CH:12]=1.[CH2:22]([CH:30]([C:36](OCC)=[O:37])[C:31](OCC)=[O:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C[O-].[Na+].S(=O)(=O)(O)O>CO>[CH2:22]([C:30]1[C:31]([OH:32])=[N:16][C:15]([C:14]2[CH:18]=[CH:19][C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:3])[CH2:20][CH3:21])=[CH:12][CH:13]=2)=[N:17][C:36]=1[OH:37])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 252340Diethyl octylmalonateHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 70415390HCID 70415390, compound

Product 1

HCID 178418516HCID 178418516, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pour 1.15 g sodium metal, and 33 ml dry methanol into 100 ml four-mouth flask; add 5 g of optically active (s)-4-(6-methyloctyloxy)benzamidine hydrochloric acid salt, then pour 4.55 g of diethyl n-octylmalonate into this sodium methylate solution and then allow to react for 18 hours under heat and reflux conditions. After cooling, acidify the mixture utilizing concentrated sulfuric acid, and extract the crystals. The impure crystals are purified, and then optically active 6.32 g of (s)-5-n-octyl-2-[4-(6methyloctyloxy)phenyl]-4,6-dihydroxy-pyrimidine is obtained.

Workup

  1. customto react for 18 hours
  2. temperatureunder heat
  3. temperaturereflux conditions
  4. temperatureAfter cooling
  5. extractionextract the crystals
  6. customThe impure crystals are purified

Sources & evidence

ORD record
ord-1ff5c11c42b04a318b57cf8f518bbb02
Source dataset
uspto-grants-1988_02
Patent number
US04725688

Reaction notes

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