Hydrochloric Acid → HCID 178509540, compound

HRID 2422453Notes

Reaction equation

HRID 2422453 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1Cl)[C:5]#[N:6].[K+].C(O[C:15]([S-:17])=[S:16])C.Cl>CN(C=O)C>[SH:17][C:15]1[S:16][C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1044643-Amino-4-chlorobenzonitrileHCID 2735045Potassium ethylxanthate

Product 1

HCID 178509540HCID 178509540, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 3-amino-4-chloro-benzonitrile (Example 251, 9.0 g, 59 mmol) in 90 mL of DMF was added O-ethylxanthic acid potassium salt (Aldrich, 21.23 g, 133 mmol). The mixture was heated to 115° C. for 4 h. After cooled to room temperature, the mixture was diluted with ice/water and was acidified to pH 2 with 2N HCl. Filtration followed by washing with water gave a crude product, which was recrystallized from EtOH/water to give 5.6 g (49%) of product. 1H NMR (400 MHz, DMSO-d6) δ 14.10 (br s, 1H), 7.90 (d, J=8.3 Hz, 1H), 7.69 (dd, J=8.3, 1.1 Hz, 1H), 7.60 (s, 1H). MS (EI): m/z 191 (M−H).

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationFiltration
  3. washby washing with water
  4. customgave a crude product, which
  5. customwas recrystallized from EtOH/water

Sources & evidence

ORD record
ord-90b8f2e5c8aa4d408eaa478b735fd571
Source dataset
uspto-grants-2011_06
Patent number
US07960408B2

Reaction notes

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