Ethanol → HCID 178513711, compound

HRID 1405154Notes

Reaction equation

HRID 1405154 reaction equation
[C:1]([C:3](=[C:7](SC)SC)[C:4]([NH2:6])=O)#[N:2].[CH:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1.[OH2:26].[NH2:27][NH2:28].[CH3:29][CH2:30][OH:31]>>[CH2:18]([C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:7]2[C:3]([C:1]([NH2:2])=[O:26])=[C:4]([NH:6][CH2:18][C:15]3[CH:14]=[CH:13][C:30]([OH:31])=[CH:29][CH:16]=3)[NH:28][N:27]=2)=[CH:23][CH:24]=1)[C:15]1[CH:14]=[CH:13][CH:12]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 136914Benzenamine, 4-(phenylmethyl)-HCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 178513711HCID 178513711, compound

Conditions

Temperature
75 °C

Procedure

Dissolved 0.500 g 2-cyano-3,3-bis(methylthio)acrylamide in 15 mL EtOH and added 4-Aminodiphenylmethane (1.0 eq.). Stirred reaction at 75° C. until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75° C. until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain a yellow powder as product. Product was allowed to dry under vacuum for 1 hr.

Workup

  1. customreaction at 75° C.
  2. customOnce complete (18 hrs), reaction
  3. customwas brought to room temperature
  4. filtrationfiltered
  5. customto obtain a light yellow powder as product
  6. customto dry under vacuum for 1 hr
  7. customReaction
  8. custom(18 hrs), reaction
  9. customwas brought to room temperature
  10. filtrationfiltered
  11. customto obtain a yellow powder as product
  12. customto dry under vacuum for 1 hr

Sources & evidence

ORD record
ord-2317639e433847ffb6132d3b983cf760
Source dataset
uspto-grants-2014_12
Patent number
US08916555B2

Reaction notes

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