Tetrahydrofuran → N-(4-(1-adamantyl)-2-methylphenyl)-2-bromo-5-nitrobenzamide

HRID 719759Notes

Reaction equation

HRID 719759 reaction equation
O1CCCC1.Cl.[C:7]12([C:17]3[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([CH3:24])[CH:18]=3)[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.C(N(CC)CC)C.[Br:32][C:33]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][C:34]=1[C:35](Cl)=[O:36]>O>[C:7]12([C:17]3[CH:23]=[CH:22][C:20]([NH:21][C:35](=[O:36])[C:34]4[CH:38]=[C:39]([N+:42]([O-:44])=[O:43])[CH:40]=[CH:41][C:33]=4[Br:32])=[C:19]([CH3:24])[CH:18]=3)[CH2:14][CH:13]3[CH2:15][CH:9]([CH2:10][CH:11]([CH2:12]3)[CH2:16]1)[CH2:8]2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 114710722-Bromo-5-nitrobenzoyl chlorideHCID 163762694-(1-Adamantanyl)-2-methylaniline hydrochloride

Product 1

HCID 12087761N-(4-(1-adamantyl)-2-methylphenyl)-2-bromo-5-nitrobenzamideYield 61.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 mL of a tetrahydrofuran solution comprising 300 mg of 4-(1-adamantyl)-2-methylaniline hydrochloride and 120 mg of triethylamine, 5 mL of a tetrahydrofuran solution comprising 290 mg of 2-bromo-5-nitrobenzoylchloride was dropwise added under cooling with ice. After stirring for about 30 minutes, water was added thereto, and the precipitated crystals were collected by filtration. The collected crystals were washed with water and then dried to obtain 310 mg of N-(4-(1-adamantyl)-2-methylphenyl)-2-bromo-5-nitrobenzamide (Compound No. 46) having a melting point of 229° C.

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling with ice
  3. filtrationthe precipitated crystals were collected by filtration
  4. washThe collected crystals were washed with water
  5. customdried

Sources & evidence

ORD record
ord-52d2133bd8a448888326e6b4e0a98ac0
Source dataset
uspto-grants-2006_11
Patent number
US07132546B2

Reaction notes

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