p-Toluenesulphonyl cyanide → HCID 25100915, compound

HRID 1404949Notes

Reaction equation

HRID 1404949 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)=[O:13].S([C:34]#[N:35])(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[N:14]1([C:12](=[O:13])[CH2:11][S:10][C:2]2[N:3]([C:34]#[N:35])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 87946p-Toluenesulphonyl cyanideHCID 1519932HCID 1519932, compound

Product 1

HCID 25100915HCID 25100915, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of compound 16 (0.52 g, 1.6 mmol, 1.0 eq) in 6 mL of dry THF stirred at −78° C. under N2 LiHMDS (1.7 mL, 1.05 eq) was added. The mixture was stirred for 15 min. at −78° C. and then TosCN (306 mg, 1.05 eq. in 1 mL of THF) was added dropwise. The reaction mixture was quickly allowed to warmed up to RT. The reaction mixture was quenched with 10 mL of NH4Cl (sat.), extracted into ethyl acetate, washed with brine and concentrated to give creamy solid. The crude was purified by column chromatography (ethyl acetate/hexanes) to give 79 (330 mg, 59%). MP=153.3-154.2° C. Anal/Calcd. for C19H16H4OS: C, 65.50; H, 4.63; N, 16.08; S, 9.20. Found C, 65.59; H, 4.66; N, 16.06; S, 9.16.

Workup

  1. additionwas added
  2. temperatureto warmed up to RT
  3. customThe reaction mixture was quenched with 10 mL of NH4Cl (sat.)
  4. extractionextracted into ethyl acetate
  5. washwashed with brine
  6. concentrationconcentrated
  7. customto give creamy solid
  8. customThe crude was purified by column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-feb0b2bfaf444e20952c79fae6c12fda
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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