Potassium Cyanide → 2-Cyano-6-butylaminobenzothiazole

HRID 604234Notes

Reaction equation

HRID 604234 reaction equation
[C-:1]#[N:2].[K+].Cl[C:5]1[S:6][C:7]2[CH:13]=[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:8]=2[N:9]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O>[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:8]=2[N:9]=1)#[N:2]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 62657Potassium Phosphate, TribasicHCID 670401982-Chloro-6-butylaminobenzothiazole

Product 1

HCID 670406702-Cyano-6-butylaminobenzothiazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Potassium cyanide (18 mg) and 2-chloro-6-butylaminobenzothiazole (18 mg) were dissolved in 1 ml DMSO and heated to 120° C. for 4 h. After cooling to room temperature, the reaction was poured into 0.2M potassium phosphate, pH 4.5. The aqueous layer was extracted with ethyl acetate three times, washed with water, and dried over sodium sulfate. The solvent was removed by rotary evaporation and the residue purified by silica gel chromatography (20% ethyl acetate in hexanes). 1H-NMR (d6-DMSO): δ 7.84 (d, 1H, 3=8.8 Hz), 7.14 (d, 1H, 3=2.4 Hz), 6.99 (dd, 1H, 3=2.4, 9.2 Hz), 6.67 (br t, 1H), 3.06 (m, 2H), 1.55 (m, 2H), 1.39 (m, 2H), 0.90 (t, 3H, 3=7.4 Hz).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate three times
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed by rotary evaporation
  6. customthe residue purified by silica gel chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b39ae4b17b144d12ba0ebc03c32866ba
Source dataset
uspto-grants-2011_03
Patent number
US07910087B2

Reaction notes

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