Benzyl mercaptan → HCID 54185340, compound

HRID 1638981Notes

Reaction equation

HRID 1638981 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([C:13]1[C:14](=[O:38])[NH:15][C:16](=[O:37])[N:17]([CH:36]=1)[C@@H:18]1[O:35][C@H:22]([CH2:23]OS(C2C=CC(C)=CC=2)(=O)=O)[C@@H:20]([OH:21])[CH2:19]1)[CH3:12]>CN(C)C=O>[CH2:1]([S:8][CH2:23][C@H:22]1[O:35][C@@H:18]([N:17]2[CH:36]=[C:13]([CH2:11][CH3:12])[C:14](=[O:38])[NH:15][C:16]2=[O:37])[CH2:19][C@@H:20]1[OH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 5280128HCID 5280128, compound

Product 1

HCID 54185340HCID 54185340, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 0.5 g of benzyl mercaptan in 10 ml of dry dimethylformamide was treated with 60 mg of a 80% dispersion of sodium hydride in mineral oil. After the effervescence had ceased a solution of 1.64 g of 2'-deoxy-5-ethyl-5'-O-(p-toluenesulphonyl)uridine in 20 ml of dry dimethylformamide was added. The mixture was stirred and heated at 100° C. under a nitrogen gas atmosphere. The course of the reaction was followed by thin layer chromatography. After 4 hours the mixture was evaporated to give an oily residue. This was purified by flash column chromatography on silica gel using methanol/dichloromethane (1:9) for the elution. The fractions containing the product were combined and evaporated to yield an oil which solidified and was recrystallized from diethyl ether to give 1.46 g of 5'-benzylthio-2',5'-dideoxy-5-ethyluridine, mp 149°-151° C.

Workup

  1. additionwas added
  2. customAfter 4 hours the mixture was evaporated
  3. customto give an oily residue
  4. customThis was purified by flash column chromatography on silica gel
  5. washfor the elution
  6. additionThe fractions containing the product
  7. customevaporated
  8. customto yield an oil which
  9. customwas recrystallized from diethyl ether

Sources & evidence

ORD record
ord-d0f60e6bd21343b28405df8bc23919bd
Source dataset
uspto-grants-1989_11
Patent number
US04882316

Reaction notes

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