N-bromobutanimide → HCID 178444054, compound

HRID 542705Notes

Reaction equation

HRID 542705 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]2[N:4]([N:5]=[C:6]([CH2:10][CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:45])[CH:21]([O:28][C:29]4[CH:34]=[CH:33][C:32]([C:35]([CH2:38][CH3:39])([CH3:37])[CH3:36])=[CH:31][C:30]=4[C:40]([CH2:43][CH3:44])([CH3:42])[CH3:41])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:15][CH:14]=3)[NH:7]2)[N:3]=1.[Br:46]N1C(=O)CCC1=O>O1CCCC1.ClCCl>[Br:46][C:9]1[C:2]([CH3:1])=[N:3][N:4]2[C:8]=1[NH:7][C:6]([CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:45])[CH:21]([O:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]([CH2:38][CH3:39])([CH3:36])[CH3:37])=[CH:31][C:30]=3[C:40]([CH2:43][CH3:44])([CH3:42])[CH3:41])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][CH:18]=1)=[N:5]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178444055HCID 178444055, compound

Product 1

HCID 178444054HCID 178444054, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 100 ml of tetrahydrofuran and 500 ml of dichloromethane was dissolved 50.0 g of 6-methyl-2-(3-(4-(2-(2,4-di-tert-amylphenoxy)octaneamido)phenyl)propyl)-1H-pyrazolo(1,5-b)(1,2,4)triazole (J). Thereto, 13.8 g of N-bromosuccinimide was added at room temperature, and stirring was continued for 30 minutes. The resulting reaction mixture was washed with 500 ml each of water for three times, and dried over anhydrous magnesium sulfate. An oily substance obtained by removing the solvent from the reaction mixture by distillation under reduced pressure was fractionated by chromatography on a column of silica gel (eluting solvent; hexane-ethyl acetate (3/1) mixture), and the eluate was concentrated and evaporated to dryness. Thus, the desired intermediate (K), 7-bromo-6-methyl-2-(3-(4-(2-(2,4-di-tert-amylphenoxy)octaneamido)phenyl)propyl)-1H-pyrazolo(1,5-b)(1,2,4)triazole, was obtained. Yield: 49.3 g (87%).

Workup

  1. customThe resulting reaction mixture
  2. washwas washed with 500 ml each of water for three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAn oily substance obtained
  5. customby removing the solvent from the reaction mixture
  6. distillationby distillation under reduced pressure
  7. concentrationthe eluate was concentrated
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-035c0271dcfb4e3bbba819c73a3b2f2b
Source dataset
uspto-grants-1987_04
Patent number
US04659652

Reaction notes

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