4-((5-Bromopyrimidin-2-yl)thio)aniline → 1-(4-(5-Bromopyrimidin-2-ylsulfanyl)phenyl)-3-(2-nitrobenzoyl)urea

HRID 736329Notes

Reaction equation

HRID 736329 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([N:8]=[C:9]=[O:10])=[O:7])([O-:3])=[O:2].[Br:15][C:16]1[CH:17]=[N:18][C:19]([S:22][C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)=[N:20][CH:21]=1>O1CCOCC1.O>[Br:15][C:16]1[CH:17]=[N:18][C:19]([S:22][C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=3[N+:1]([O-:3])=[O:2])=[O:10])=[CH:27][CH:28]=2)=[N:20][CH:21]=1

Participants

5

Reactant 2

HCID 27610434-((5-Bromopyrimidin-2-yl)thio)anilineHCID 125834382-Nitrobenzoyl isocyanate

Product 1

HCID 113174691-(4-(5-Bromopyrimidin-2-ylsulfanyl)phenyl)-3-(2-nitrobenzoyl)ureaYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2-nitrobenzoyl isocyanate (3 g, 0.016 mol) in dry 1,4-dioxane (15 mL) was added dropwise to a solution of 4n (2.93 g, 0.01 mol) in dry 1,4-dioxane (15 mL) with stirring at room temperature. The reaction mixture was stirred for 18 hours and then diluted with water. The precipitated solid was collected by filtration and washed with water. The solid was dissolved in ethyl acetate, and the organic layer was washed with water 2-3 times, dried, and concentrated to give 1-[4-(5-bromopyrimidin-2-ylsulfanyl)-phenyl]-3-(2-nitrobenzoyl)urea (6n), yield 92%. 1H NMR (400 MHz, DMSO-d6): δ 11.32 (br, s, 1H), 10.35 (br, s, 1H), 8.78 (s, 2H), 8.22 (m, 1H), 7.91 (m, 1H), 7.77 (m, 2H), 7.67 (m, 2H), 7.57 (m 2H); EI-MS m/z 473 [M]+, 475 [M+2]+; HRMS calculated for C18H12BrN5O4SNa [M+Na]+:495.9685, found: 495.9701. Anal. (C18H12BrN5O4S) C, H, N.

Workup

  1. stirringThe reaction mixture was stirred for 18 hours
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. dissolutionThe solid was dissolved in ethyl acetate
  5. washthe organic layer was washed with water 2-3 times
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d1e86a0cc51f4e3580d8ce315c4290bc
Source dataset
uspto-grants-2009_09
Patent number
US07595326B2

Reaction notes

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