Sodium Cyanide → HCID 178420123, compound

HRID 2249598Notes

Reaction equation

HRID 2249598 reaction equation
S([CH2:11][N+:12]#[C-:13])(C1C=CC(C)=CC=1)(=O)=O.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=O.[C-]#N.[Na+].O1CC[N:27]=C1>C(O)C>[NH:12]1[CH:13]=[C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)[N:27]=[CH:11]1

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 142732-PyridinecarboxaldehydeHCID 68157OxazolineHCID 161915Tosylmethyl isocyanide

Product 1

HCID 178420123HCID 178420123, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
15 °C

Procedure

This compound known in the literature was made by an alternative route in analogy to Heterocycles 1994, 39 (1), 139: Tosylmethylisocyanide (TOSMIC) (3.57 g) was suspended in ethanol (50 ml) and 2-picolinealdehyde (2.0 g) was added. Sodium cyanide (92 mg) was added in one portion at 15° C. and the mixture was allowed to stir—the internal temperature rose to 26° C. and a clear solution was obtained. The mixture was cooled again to 15° C. and the intermediate oxazoline derivative precipitated. The suspension was filtered and the solid intermediate was washed with ether/hexanes 1:1 and dried in vacuo (yield: 4.77 g).

Workup

  1. customrose to 26° C.
  2. customa clear solution was obtained
  3. filtrationThe suspension was filtered
  4. washthe solid intermediate was washed with ether/hexanes 1:1
  5. customdried in vacuo (yield: 4.77 g)

Sources & evidence

ORD record
ord-abd65d3fbee94cc68c93b80e111fb7c8
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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