N-bromobutanimide → HCID 53955893, compound

HRID 1018664Notes

Reaction equation

HRID 1018664 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][CH:8]1[C:14]2[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:35])C(=O)C1>CC#N>[C:1]([O:5][C:6](=[O:27])[NH:7][CH:8]1[C:14]2[CH:15]=[C:16]([Br:35])[C:17]([O:19][CH2:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10595534HCID 10595534, compound

Product 1

HCID 53955893HCID 53955893, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (2-cyclohexylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-yl)-carbamic acid tert-butyl ester (7.93 g, 21.2 mmol) in CH3CN (300 mL) was added NBS (3.96 g, 22.3 mmol). The mixture was stirred for 1.5 h, then blown dry under a stream of N2. The residue was resuspended in CCl4, filtered, and concentrated to a solid. The solid was recrystallized from CH3CN to yield a white solid (8.5 g, 88%). MS [M−H]− 452, m.p. 142-144° C.

Workup

  1. dry with materialblown dry under a stream of N2
  2. filtrationfiltered
  3. concentrationconcentrated to a solid
  4. customThe solid was recrystallized from CH3CN

Sources & evidence

ORD record
ord-0fc44c8ea3a04c409b842da3690c0d27
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

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