Triethylamine → HCID 10523080, compound

HRID 2187668Notes

Reaction equation

HRID 2187668 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(C1NC=CN=1)(C1NC=CN=1)=O.[Br:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH2:34])=[CH:28][CH:27]=1.C(N(CC)CC)C>C1COCC1>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH:34][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:11][CH3:12])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 769705-Chloro-o-anisic acidHCID 533915p-BromophenethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 10523080HCID 10523080, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.3 g (44.4 mmol) of 5-chloro-2-methoxybenzoic acid and 7.8 g (48.1 mmol) of carbonylbisimidazole in 200 ml of absolute THF was stirred at room temperature for 2 h. 7.7 ml (50.0 mmol) of 2-(4-bromophenyl)ethylamine and 10 ml of triethylamine were added and the resulting solution was stirred at room temperature for 24 h. The reaction solution was then poured onto water, and the deposited precipitate was filtered off with suction and washed with water. Drying of the precipitate yielded 15.8 g of the title compound in the form of a slightly yellow-colored solid. M.p.: 104-109° C. Rf (silica gel, EA/heptane 2:1)=0.66. MS (ESI): m/z=368/370 (M+H)+.

Workup

  1. additionThe reaction solution was then poured onto water
  2. filtrationthe deposited precipitate was filtered off with suction
  3. washwashed with water
  4. customDrying of the precipitate

Sources & evidence

ORD record
ord-5e192959dcd94b73a7c1997bc16a5231
Source dataset
uspto-grants-2002_06
Patent number
US06410573B1

Reaction notes

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