Sodium Chloride → HCID 59161750, compound

HRID 409404Notes

Reaction equation

HRID 409404 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)(=O)=O)=CC=1.[C-:27]#[N:28].[Na+].[Na+].[Cl-]>CS(C)=O>[C:27]([CH2:12][CH:13]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)#[N:28]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 59161738HCID 59161738, compound

Product 1

HCID 59161750HCID 59161750, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To 2-(tert-butoxycarbonylamino)-2-(thiophen-3-yl)ethyl 4-methylbenzenesulfonate (E2) in DMSO was added NaCN, and the solution was heated to 90° C. for 2 hours. The reaction was cooled, poured into NaCl (sat), and extracted with EtOAc. The organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 25% EtOAc/Hexanes) gave pure tert-butyl 2-cyano-1-(thiophen-3-yl)ethylcarbamate (E3).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe organics were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-12ef191fc9074a81876ecfda1ee52c96
Source dataset
uspto-grants-2014_06
Patent number
US08759388B2

Reaction notes

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