m-Chloroperbenzoic acid → HCID 18792758, compound

HRID 1004596Notes

Reaction equation

HRID 1004596 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[C:22]([F:30])[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[CH:26]4)=[CH:24][C:18]=3[N:17]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].ClC1C=CC=C(C(OO)=[O:39])C=1.[K+].[Br-]>ClCCl>[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:16]2[NH:20][C:19]3[CH:21]=[C:22]([F:30])[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[CH:26]4)=[CH:24][C:18]=3[N:17]=2)=[O:39])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 253877Potassium BromideHCID 18792760HCID 18792760, compound

Product 1

HCID 18792758HCID 18792758, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (0.24 g, 45%) was prepared by the above general procedure using 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(imidazol-1-yl)-1H-benzimidazole (0.5 g, 1.14 mmol) (obtained in example 2), m-chloroperbenzoic acid (50%, 0.47 g, 1.4 mmol) and dichloromethane (10 mL). mp 234-235° C.; IR (KBr) 3449, 1049 cm- 1; 1H NMR (CD3OD+CDCl3) δ 2.28 (s, 3H, CH3), 4.42 (q,J=6.3 Hz, 2H, OCH2CF3), 4.74 (ABq, J=9.6 Hz, Δv=6.2 Hz, 2H, SOCH2), 6.74 (d,J=5.6 Hz, 1H), 7.20 (m, 2H), 7.52 (d,J=10.8 Hz, 1H), 7.70 (d,J=7.6 Hz, 1H), 7.86 (s, 1H), 8.30 (d,J=5.6 Hz, 1H); Mass (m/z) 453 (M+).

Sources & evidence

ORD record
ord-9afb8261cd344184a67b3aaff51b7826
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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