Sodium Cyanide → 5-(2-Cyano-1,1-dimethylethyl)-2-methylamino-1,3,4-thiadiazole

HRID 436683Notes

Reaction equation

HRID 436683 reaction equation
Cl[CH2:2][C:3]([C:6]1[S:10][C:9]([NH:11][CH3:12])=[N:8][N:7]=1)([CH3:5])[CH3:4].[C-:13]#[N:14].[Na+]>CS(C)=O>[C:13]([CH2:2][C:3]([C:6]1[S:10][C:9]([NH:11][CH3:12])=[N:8][N:7]=1)([CH3:5])[CH3:4])#[N:14]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 127696565-(1-Chloro-2-methylpropan-2-yl)-N-methyl-1,3,4-thiadiazol-2-amine

Product 1

HCID 214309265-(2-Cyano-1,1-dimethylethyl)-2-methylamino-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 20.5 g. portion of the intermediate prepared in Example 1 and 10 g. of NaCN were added to 50 ml. of dimethylsulfoxide and heated at 110° C. for two hours. The reaction mixture was then cooled and poured into 300 ml. of water, which was then extracted with a total of 1 liter of ethyl ether. The combined ether extracts were dried over anhydrous Na2SO4, filtered, and evaporated to dryness yielding a dark oil. The oil was chromatographed on a silica gel column, eluting with ethyl acetate. The desired intermediate product, 5-(2-cyano-1,1-dimethylethyl)-2-methylamino-1,3,4-thiadiazole, m.p. 65°-67° C., was isolated in the amount of 750 mg.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. additionpoured into 300 ml
  3. extractionof water, which was then extracted with a total of 1 liter of ethyl ether
  4. dry with materialThe combined ether extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customyielding a dark oil
  8. customThe oil was chromatographed on a silica gel column
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d9f607598d5b4f118e071ff584f4083e
Source dataset
uspto-grants-1977_06
Patent number
US04028090

Reaction notes

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