Water → HCID 178433378, compound

HRID 2387907Notes

Reaction equation

HRID 2387907 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([S:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16]Cl)=[CH:12][CH:11]=2)=[C:4]([CH3:18])[N:3]=1.[C-:19]#[N:20].[K+].O>CN(C=O)C.CS(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([S:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:19]#[N:20])=[CH:12][CH:11]=2)=[C:4]([CH3:18])[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 178433377HCID 178433377, compound

Product 1

HCID 178433378HCID 178433378, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from step (ii) (8.7 g) and KCN (8.28 g) in DMF (20 ml) and DMSO (20 ml) was stirred at rt for 2 h then 50° C. for 2 h. Water (150 ml) was added and stirred for 30 min. The solid obtained was filtered off and added to MeOH (150 ml), heated to reflux for 5 min then hot filtered and allowed to cool to rt. The precipitate was filtered and dried under high vacuum at 45° C., to give the subtitle compound as a brown solid, 23 g.

Workup

  1. wait50° C. for 2 h
  2. stirringstirred for 30 min
  3. customThe solid obtained
  4. filtrationwas filtered off
  5. additionadded to MeOH (150 ml)
  6. temperatureheated
  7. temperatureto reflux for 5 min
  8. filtrationthen hot filtered
  9. temperatureto cool to rt
  10. filtrationThe precipitate was filtered
  11. customdried under high vacuum at 45° C.

Sources & evidence

ORD record
ord-114229a016114a91a22023586dfd1f6d
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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