Sodium Carbonate → 1-[4-(5-Bromopyrimidine-2-sulfinyl)phenyl]-3-(2-nitrobenzoyl)-urea

HRID 736331Notes

Reaction equation

HRID 736331 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19](=[O:29])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:26]([O-:28])=[O:27])=[O:17])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:38])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([S:8]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([NH:18][C:19](=[O:29])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:26]([O-:28])=[O:27])=[O:17])=[CH:13][CH:14]=2)=[O:38])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 113174691-(4-(5-Bromopyrimidin-2-ylsulfanyl)phenyl)-3-(2-nitrobenzoyl)urea

Product 1

HCID 115476771-[4-(5-Bromopyrimidine-2-sulfinyl)phenyl]-3-(2-nitrobenzoyl)-ureaYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6n (1.0 g, 2.11 mmol) in DCM (50 mL) at 0° C. was added MCPBA (0.364 g, 2.11 mmol) in portions. The resulting mixture was stirred at room temperature for 6 h and then diluted with water and made slightly basic with Na2CO3 solution. The DCM layer was separated, and the aqueous layer was extracted with DCM. The combined organic layers were dried and evaporated to give a residue that was purified by silica gel flash column chromatography (ethyl acetate-methanol 5:1) to give 8g, yield 48%. 1H NMR (400 MHz, DMSO-d6): δ 11.32 (br, s, 1H), 10.38 (br, s, 1H), 9.15 (s, 2H), 8.20 (m, 1H), 7.88 (m, 1H), 7.72-7.80 (m, 6H); EI-MS m/z 489 [M]+, 491 [M+2]+; HRMS calculated for C18H12BrN5O5SNa [M+Na]+: 511.9634, found: 511.9632. Anal. (C18H12BrN5O5S) C, H, N.

Workup

  1. customThe DCM layer was separated
  2. extractionthe aqueous layer was extracted with DCM
  3. customThe combined organic layers were dried
  4. customevaporated
  5. customto give a residue that
  6. customwas purified by silica gel flash column chromatography (ethyl acetate-methanol 5:1)

Sources & evidence

ORD record
ord-5e4a5c354b034f62b7f8e3d302a6cf1b
Source dataset
uspto-grants-2009_09
Patent number
US07595326B2

Reaction notes

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