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

HRID 1966199
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HRID 1966199 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-45f04fb846a741a2a95b2a68088b532e
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08420642B2

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