2-Cyanoethanethioamide → HCID 178458231, compound

HRID 2362823Notes

Reaction equation

HRID 2362823 reaction equation
[Si:1]([O:8][CH:9]([CH3:20])[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:21]([CH2:23][C:24]([NH2:26])=[S:25])#[N:22]>C(O)C>[NH2:26][C:24]1[C:23]([C:21]#[N:22])=[C:16]([C:15]2[CH:18]=[CH:19][C:12]([O:11][CH2:10][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH3:20])=[CH:13][CH:14]=2)[C:23]([C:21]#[N:22])=[C:24]([SH:25])[N:26]=1

Participants

4

Reactant 2

HCID 14162772-CyanoethanethioamideHCID 592019704-(2-{[tert-Butyl(dimethyl)silyl]oxy}propoxy)benzaldehyde

Product 1

HCID 178458231HCID 178458231, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.77 g (5.99 mmol) of the compound from Example 41A and 1.26 g (12.59 mmol) of cyanothioacetamide in 25 ml of ethanol is stirred at +78° C. for 6 h. The mixture is then cooled to RT and stirred at this temperature for a further 20 h. The resulting precipitate is filtered off with suction and washed with cold diethyl ether. Further product is obtained from the concentrated filtrate solution by chromatographic purification on silica gel 60 (mobile phase gradient cyclohexane/ethyl acetate 1:1→1:4).

Workup

  1. filtrationThe resulting precipitate is filtered off with suction
  2. washwashed with cold diethyl ether
  3. customFurther product is obtained from the concentrated filtrate solution by chromatographic purification on silica gel 60 (mobile phase gradient cyclohexane/ethyl acetate 1:1→1:4)

Sources & evidence

ORD record
ord-e6df32c03e6e4fce828a081cf8247103
Source dataset
uspto-grants-2014_04
Patent number
US08691850B2

Reaction notes

Loading…