Benzoyl isothiocyanate → HCID 58033240, compound

HRID 712175Notes

Reaction equation

HRID 712175 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Br:9])[N:3]=1.[C:10]([N:18]=[C:19]=[S:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:19]([NH:18][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[S:20])[CH:5]=[C:4]([Br:9])[N:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanate2×HCID 140910412,6-Dibromopyridin-4-amine

Product 1

HCID 58033240HCID 58033240, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,6-dibromopyridin-4-amine in THF (250 mL) was added benzoylisothiocyanate (3.50 mL, 26.0 mmol)) and the resulting reaction mixture heated to 70° C. for 16 h. A further 1.50 mL (11.20 mmol) of benzoylisothiocyanate was added to complete the reaction and the reaction stirred at 70° C. for 16 h. After completion (by TLC), the solvent was distilled under reduced pressure, the residue treated with 10% MeOH-ether solution then filtered to obtain the desired product as a yellow solid (7.60 g, 85%).

Workup

  1. customthe resulting reaction mixture
  2. customthe reaction
  3. distillationAfter completion (by TLC), the solvent was distilled under reduced pressure
  4. additionthe residue treated with 10% MeOH-ether solution
  5. filtrationthen filtered

Sources & evidence

ORD record
ord-c0915ee75f7b4b318cb8f5c1f3eb47c3
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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