Triethylamine → HCID 19438777, compound

HRID 1733870Notes

Reaction equation

HRID 1733870 reaction equation
[N:1]1([C:6]2[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[C:20](Cl)([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:21]>O1CCCC1>[C:20]([NH:10][C:9]1[CH:11]=[CH:12][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:7][CH:8]=1)([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 3201654-(1H-imidazol-1-yl)aniline

Product 1

HCID 19438777HCID 19438777, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1H-imidazol-1-yl)-aniline (14 g; ~88.2 mmol) in 400 ml dry tetrahydrofuran was added dry triethylamine (14.0 ml; ~102 mmol). Ethoxalyl chloride (11.2 ml; 100 mmol) was added dropwise and the reaction mixture was stirred for 2 h. The solvent was removed under reduced pressure, and the residue was stirred with water to give the title compound (19.2 g; 85%). M.p. 177°-180° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. stirringthe residue was stirred with water

Sources & evidence

ORD record
ord-6b45d05e5040466e8db82230550cb755
Source dataset
uspto-grants-1996_07
Patent number
US05532236

Reaction notes

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