Potassium Cyanide → 2-Cyano-6-ethylaminobenzothiazole

HRID 1511491Notes

Reaction equation

HRID 1511491 reaction equation
[C-:1]#[N:2].[K+].Cl[C:5]1[S:6][C:7]2[CH:13]=[C:12]([NH:14][CH2:15][CH3:16])[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][CH3:16])[CH:11]=[CH:10][C:8]=2[N:9]=1)#[N:2]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 62657Potassium Phosphate, TribasicHCID 670401072-Chloro-6-ethylaminobenzothiazole

Product 1

HCID 670407172-Cyano-6-ethylaminobenzothiazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Potassium cyanide (18 mg) and 2-chloro-6-ethylaminobenzothiazole (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 7.85 (d, 1H, J=9.2 Hz), 7.13 (d, 1H, J=2.4 Hz), 6.98 (dd, 1H, J=2.4, 8.8 Hz), 6.44 (br t, 1H), 3.09 (m, 2H), 1.18 (t, 3H, J=7.2 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-62da027dd8ab4e78867b969337d77c93
Source dataset
uspto-grants-2012_07
Patent number
US08216550B2

Reaction notes

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