alpha-Bromo-2-nitrotoluene → HCID 10225207, compound

HRID 1297137Notes

Reaction equation

HRID 1297137 reaction equation
[CH2:1]([O:3][C:4]1[C:22]([O:23][CH3:24])=[CH:21][C:7]2[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:9][CH2:10][C:11](=[O:14])[N:12]([CH3:13])[C:6]=2[CH:5]=1)[CH3:2].[N+](C1C=CC=CC=1CBr)([O-])=O.Br[CH2:37][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[C:41]#[N:42]>>[CH2:1]([O:3][C:4]1[C:22]([O:23][CH3:24])=[CH:21][C:7]2[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:9][CH:10]([CH2:37][C:38]3[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=3)[C:41]#[N:42])[C:11](=[O:14])[N:12]([CH3:13])[C:6]=2[CH:5]=1)[CH3:2]

Participants

4

Reactant 3

HCID 77569alpha-Bromo-2-nitrotolueneHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 9880314HCID 9880314, compound

Product 1

HCID 10225207HCID 10225207, compoundYield 35%

Procedure

By replacing 1-ethyl-7,8-dimethoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (IIbd) in example IIbh by 8-ethoxy-7-methoxy-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (IIIda), and 2-nitrobenzyl bromide by 3-bromomethyl-benzonitrile, and proceeding in the same manner, the abovenamed product is obtained. Yield: 35%. M: 148–150° C. 1H-NMR (CDCl3, 200 MHz): d 1.53 (s, 3H, CH3), 3.40 (s, 3H, NCH3), 3.58–3.62 (m, 2H, 1H —CH2Ph+CH), 3.72 (s, 3H, OCH3), 3.75–3.80 (m, 1H CH2Ph), 4.17 (q, 2H, CH2), 6.66 (s, 1H Ar), 6.76 (s, 1H Ar), 7.35–7.67 (m, 9H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom148–150° C

Sources & evidence

ORD record
ord-bb5efe12cdc34e48af0de111746ace6a
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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