Sodium hydride → HCID 86701217, compound

HRID 472271Notes

Reaction equation

HRID 472271 reaction equation
[H-].[Na+].O1CCOCC1.[Br:9][C:10]1[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=1.[N:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[C:18]=[S:19]>[Cl-].[NH4+]>[Br:9][C:10]1[C:11]([NH:16][C:18]([NH:17][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[S:19])=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 312751,4-DioxaneHCID 752934-Methoxyphenyl isothiocyanateHCID 8177002-Amino-3-bromopyridine

Product 1

HCID 86701217HCID 86701217, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a suspension of sodium hydride, 60% disp. in mineral oil (3:2, sodium hydride: mineral oil, 1.0 g, 25 mmol) in 1,4-dioxane (50 mL, 600 mmol) was added 3-bromo-pyridin-2-ylamine (2.68 g, 15.5 mmol). The mixture was stirred for 5 minutes at room temperature under an atmosphere of nitrogen. 1-Isothiocyanato-4-methoxy-benzene (2.35 mL, 17.0 mmol) was slowly added to the suspension. Slow gas evolution was noted and the suspension slowly thickened to a slurry. The mixture was stirred at room temperature for 18 hours and the volatiles were evaporated to a yield a tan solid. To the solid was added saturated aqueous ammonium chloride solution (100 mL). Gas evolution and exotherm noted. The mixture was stirred for 30 minutes and the waxy solid was filtered. The solid was triturated with ether (50 mL), filtered and rinsed with ether. 1-(3-Bromo-pyridin-2-yl)-3-(4-methoxy-phenyl)-thiourea was isolated as a yellow solid (4.96 g, 95%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 12.85 (s, 1H), 8.75 (s, 1H), 8.38 (dd, J=4.8, 1.2 HZ, 1H), 8.24 (dd, J=7.9, 1.3 Hz, 1H), 7.56-7.50 (m, 2H), 7.15 (dd, J=7.9, 4.9 Hz, 1H), 7.00-6.95 (m, 2H), 3.77 (s, 3H). MS=338, 340 (MH)+.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. customthe volatiles were evaporated to
  3. customa yield a tan solid
  4. stirringThe mixture was stirred for 30 minutes
  5. filtrationthe waxy solid was filtered
  6. customThe solid was triturated with ether (50 mL)
  7. filtrationfiltered
  8. washrinsed with ether

Sources & evidence

ORD record
ord-1f29e99d65cf4a6d905112df5c94f32c
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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