N-bromobutanimide → HCID 69284251, compound

HRID 748574Notes

Reaction equation

HRID 748574 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][NH:12][C:13]2[N:18]=[C:17]([O:19][CH3:20])[N:16]=[C:15]([O:21][CH3:22])[N:14]=2)[N:4]=1.BrN1C(=O)CCC1=O>C(#N)C>[CH3:22][O:21][C:15]1[N:16]=[C:17]([O:19][CH3:20])[N:18]=[C:13]([N:12]=[N:11][C:5]2[N:4]=[C:3]([O:2][CH3:1])[N:8]=[C:7]([O:9][CH3:10])[N:6]=2)[N:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69285021HCID 69285021, compound

Product 1

HCID 69284251HCID 69284251, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product of Example 1a (7.4 g. 23.8 mmol) was added slowly to a stirred mixture of 20.4 g. (115 mmol) of N-bromosuccinimide and 80 mL of acetonitrile at ambient temperature. A dark orange solution formed after 2 h of stirring. A brown/orange powder was isolated by filtration. After a water-wash, the solid was dried in a desiccator to give 5.7 g (77%) of crude product. Recrystallization from acetic acid gave brick-red needles: mp 228-232° C. (dec); 1H-NMR (d6-DMSO): δ4.060 (—OCH3); (CDCl3) δ(—OCH3); 13C-NMR (CDCl3) δ(—OCH3), 173.8 (C-OMe), 176.4 (C—N═N). Anal. Cacld for C10H12N8: C, 38.96; H, 3.92; N, 36.35. Found: C, 38.78; H, 3.94; N, 36.02.

Workup

  1. customat ambient temperature
  2. customA dark orange solution formed after 2 h
  3. customA brown/orange powder was isolated by filtration
  4. washAfter a water-wash
  5. customthe solid was dried in a desiccator

Sources & evidence

ORD record
ord-4934b4a68b464516a56036fde87e2f80
Source dataset
uspto-grants-2008_07
Patent number
US07399841B1

Reaction notes

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