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Benzoyl chloride → 1-(5-Bromopyridin-2-yl)thiourea

HRID 1966199
Notes
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Reaction equation

HRID 1966199 reaction equation
[S-:1][C:2]#[N:3].[NH4+].C(Cl)(=O)C1C=CC=CC=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1>CC(C)=O>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:2]([NH2:3])=[S:1])=[N:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 706222-Amino-5-bromopyridine

Product 1

HCID 234388741-(5-Bromopyridin-2-yl)thioureaYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1.1 Ammoniumthiocyanat (76 mmol, 1.2 eq.) is dissolved in acetone (75 ml) and benzoylchloride (1 eq.) is added dropwise. 20 min after stirring at RT, the reaction is heated to reflux. 2-Amino-5-bromopyridine (71 mmol) in acetone (50 ml) is added and 30 min heated to reflux. Afterwards, the reaction solution is poured onto ice. The precipitate is filtered and washed with water/methanol (1:1). The precipitate is dissolved in 2M NaOH (120 ml) at 80° C. and stirred 10 min at 80° C. The solution is poured into an HCl solution (5%) at 0° C. The pH of the solution is adjusted to 8 with a saturated Na2CO3 solution. The resulting precipitate is filtered and washed with water. (5-Bromo-pyridine-2-yl)-thiourea (“1”) is obtained after drying in vacuo at 40° C. as a pale yellow solid in a yield of 63%. HPLC (method C): 1.43 min; LC-MS (method A): 1.062 min, 231.95 (MH+).

Workup

  1. temperaturethe reaction is heated to reflux
  2. temperatureheated to reflux
  3. additionAfterwards, the reaction solution is poured onto ice
  4. filtrationThe precipitate is filtered
  5. washwashed with water/methanol (1:1)
  6. dissolutionThe precipitate is dissolved in 2M NaOH (120 ml) at 80° C.
  7. stirringstirred 10 min at 80° C
  8. additionThe solution is poured into an HCl solution (5%) at 0° C
  9. filtrationThe resulting precipitate is filtered
  10. washwashed with water

Sources & evidence

ORD record
ord-45f04fb846a741a2a95b2a68088b532e
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08420642B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes