m-Chloroperbenzoic acid → HCID 10031590, compound

HRID 374065Notes

Reaction equation

HRID 374065 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:42])[N:11]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][S:24][C:25]1[NH:26][C:27]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:29]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].ClC1C=CC=C(C(OO)=[O:51])C=1.S(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:42])[N:11]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][S:24]([C:25]1[NH:29][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:27]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:26]=1)=[O:51])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 71355LecimibideHCID 23665763Sodium Bisulfite

Product 1

HCID 10031590HCID 10031590, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N'-(2,4-difluorophenyl)-N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-N-heptylurea (0.59 g, 0.001 mol) in methylene chloride (50 mL) cooled to -78° was added, dropwise, a solution of metachloroperbenzoic acid (0.286 g, 0.0017 mol) in methylene chloride (10 mL). The reaction mixture was stirred at -78° for 1 hour and then allowed to warm to ambient temperature. The reaction mixture was then cooled to 0° and then added, dropwise, was a solution of saturated sodium bisulfite. The layers were separated and the organic layer was washed with saturated sodium bisulfite. The layers were separated and the sodium chloride solution dried over magnesium sulfate and concentrated under vacuum. The residue (0.76 g) was chromatographed with 1:1 hexane-ethyl acetate to give the title compound (0.43 g, 0.00071 mol) as a yellow solid, mp 77°-79°. 1H NMR (CDCl3) δ8.1-7.9(m,1H), 7.6-7.2 (m,10H), 6.9-6.7(m,2H), 6.4(d,1H,J=3.3Hz), 3.4-3.1(m,6H), 2.0-1.1(m,18H), 0.9(t,3H,J=6.4Hz).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was then cooled to 0°
  3. additionadded
  4. customThe layers were separated
  5. washthe organic layer was washed with saturated sodium bisulfite
  6. customThe layers were separated
  7. dry with materialthe sodium chloride solution dried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe residue (0.76 g) was chromatographed with 1:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-40391afbc5f9440a8af3585611fab939
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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