2-(Bromomethyl)benzonitrile → HCID 10180996, compound

HRID 2184417Notes

Reaction equation

HRID 2184417 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Br)#[N:2].[OH:11][C:12]1([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20]>>[OH:11][C:12]1([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:5][C:4]3[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=3[C:1]#[N:2])=[CH:27][CH:26]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20]

Participants

3

Reactant 2

HCID 895992-(Bromomethyl)benzonitrileHCID 10267727HCID 10267727, compound

Product 1

HCID 10180996HCID 10180996, compoundYield 71%

Procedure

The title compound is prepared in a manner analogous to the procedure set forth in Example 48 from 2-cyanobenzyl bromide and [2-hydroxy-2-(4-hydroxyphenyl)cyclohexyl][(methylethyl)sulfonyl]amine to provide 501 mg as a brown oil. This material was purified via silica gel chromatography employing the Chromatotron® using a 4000 micron rotor while eluting with a solvent of methylene chloride/ethyl acetate 9:1 to yield the title compound (291 mg, 71%) as a white solid. Ion spray M.S. 427.4 (M*−1). Calculated for C23H28N2O4S-½H2O: Theory: C 63.12, H 6.70, N 6.40. Found: C 63.20, H 6.64, N 6.28.

Workup

  1. customThe title compound is prepared in a manner analogous to the procedure
  2. customto provide 501 mg as a brown oil
  3. customThis material was purified via silica gel chromatography
  4. washwhile eluting with a solvent of methylene chloride/ethyl acetate 9:1

Sources & evidence

ORD record
ord-4d2a690fa85843c9836556a823452852
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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