Sodium hydride → HCID 53770362, compound

HRID 1856852Notes

Reaction equation

HRID 1856852 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].Br[C:15]1[N:16]=[C:17]([CH:33]2[O:37][CH2:36][CH2:35][O:34]2)[N:18]([CH2:22][C:23]2[C:31]([Cl:32])=[CH:30][C:26]3[O:27][CH2:28][O:29][C:25]=3[CH:24]=2)[C:19]=1[CH:20]=[O:21]>CN(C)C=O>[Cl:32][C:31]1[C:23]([CH2:22][N:18]2[C:19]([CH:20]=[O:21])=[C:15]([S:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:16]=[C:17]2[CH:33]2[O:37][CH2:36][CH2:35][O:34]2)=[CH:24][C:25]2[O:29][CH2:28][O:27][C:26]=2[CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14132275HCID 14132275, compoundHCID 21224857HCID 21224857, compound

Product 1

HCID 53770362HCID 53770362, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.9 g of ethyl 6-mercaptohexanoate is dissolved in 200 ml of anhydrous dimethylformamide, 1.1 g of sodium hydride at 50% in oil is added and the reaction medium is left for 20 minutes at ambient temperature. Then 7.6 g of the product obtained in Stage 4 above is added, and the whole is left overnight at ambient temperature. The dimethyl-formamide is evaporated off under vacuum, the residue is taken up in 200 ml of saturated ammonium chloride and extraction is carried out with three times 200 ml of methylene chloride. The organic phases are dried, filtered and evaporated to dryness. The residue is impasted in isopropyl ether and filtered. In this way 5.8 g of expected product (solid) is obtained.

Workup

  1. waitthe whole is left overnight at ambient temperature
  2. customThe dimethyl-formamide is evaporated off under vacuum
  3. extractionextraction
  4. customThe organic phases are dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b4730f99136e41618e47101d1a098ec7
Source dataset
uspto-grants-2000_11
Patent number
US06143774

Reaction notes

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