Sodium Cyanide → HCID 21431785, compound

HRID 436932Notes

Reaction equation

HRID 436932 reaction equation
BrCC1C=CC=C([C:9]2([C:12]([C:14]3([C:17]4[CH:18]=[C:19](CBr)[CH:20]=[CH:21][CH:22]=4)[CH2:16]C3)=[O:13])[CH2:11][CH2:10]2)C=1.[C-]#[N:26].[Na+]>CN(C)C=O>[CH:9]1([C:12]([C:14]2[CH:16]=[C:20]([CH2:21][C:22]#[N:26])[CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86734844HCID 86734844, compound

Product 1

HCID 21431785HCID 21431785, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

α-Bromo-m-tolylcyclopropyl ketone (10 g) in dry dimethylformamide (20 ml) was added dropwise during 1 hour to a stirred suspension of sodium cyanide (1.96 g) in dry dimethylformamide (40 ml). The mixture was cooled to 10° during the addition and for a further hour, then left to stand at 20° for a further 2 hours and poured onto ice (140 g). The mixture was extracted with ethyl acetate (3× 60 ml) and the extracts were combined, washed with water, dried over magnesium sulphate, filtered and evaporated to give a brown oil.

Workup

  1. temperatureThe mixture was cooled to 10° during the addition and for a further hour
  2. waitleft
  3. additionpoured onto ice (140 g)
  4. extractionThe mixture was extracted with ethyl acetate (3× 60 ml)
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a brown oil

Sources & evidence

ORD record
ord-b04f8ec819d144eaa22da29d7dd298c4
Source dataset
uspto-grants-1977_06
Patent number
US04028404

Reaction notes

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