Sodium hydrosulfide → HCID 88151774, compound

HRID 324504Notes

Reaction equation

HRID 324504 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([C:16]3[C:17]([S:23]C)=[N:18][C:19](=[O:22])[NH:20][CH:21]=3)[C:10]3[N:11]=[C:12]([CH3:14])[S:13][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:25]=1.[CH3:26][O:27][CH2:28][CH2:29]Br.CC(C)([O-])C.[K+].[SH-].[Na+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([C:16]3[C:17](=[S:23])[NH:18][C:19](=[O:22])[N:20]([CH2:29][CH2:28][O:27][CH3:26])[CH:21]=3)[C:10]3[N:11]=[C:12]([CH3:14])[S:13][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:25]=1

Participants

8

Reactant 4

HCID 28015Sodium hydrosulfideHCID 809722-Bromoethyl methyl etherHCID 23665647Potassium tert-butoxideHCID 178503574HCID 178503574, compound

Product 1

HCID 88151774HCID 88151774, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the product of example 39 step (i) (0.120 g) together with 2-bromoethyl methyl ether (0.073 ml) and a 1M solution of potassium tert-butoxide in tetrahydrofuran (0.62 ml) in N,N-dimethylformamide (3 ml) was heated at 50° C. for 20 h. Sufficient sodium hydrosulphide was added to give a blue solution and the reaction mixture heated at 80° C. for 4 h. The reaction mixture was cooled, diluted with ethyl acetate and washed with saturated aqueous ammonium chloride. The organic phase was dried over magnesium sulphate, filtered and evaporated. The crude product was purified by chromatography eluting with 1% methanol in dichloromethane, followed by trituration with ethyl acetate to give the title compound as a yellow solid.

Workup

  1. customto give a blue solution
  2. temperatureThe reaction mixture was cooled
  3. washwashed with saturated aqueous ammonium chloride
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by chromatography
  8. washeluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-7bd2ca4f6b7a4e06a8ac7f7d38531727
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

Loading…