Triethylamine → HCID 66593271, compound

HRID 1091637Notes

Reaction equation

HRID 1091637 reaction equation
[N:1]1([CH2:6][C:7]([OH:9])=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[N+:10]([C:13]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:14]=1[NH2:20])([O-:12])=[O:11].C(OP(ON1C(=O)C2C=CC=CC=2N=N1)(OCC)=O)C.C(N(CC)CC)C>C(#N)C>[NH2:20][C:14]1[CH:15]=[CH:16][C:17]([NH:19][C:7](=[O:9])[CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:18][C:13]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 656129Imidazole-1-acetic acidHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 43383702-Nitro-4-phenylenediamine

Product 1

HCID 66593271HCID 66593271, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1H-imidazole-1-ylacetic acid (284 mg, 2.25 mmol) and 2-nitrobenzene-1,4-diamine (324 mg, 2.12 mmol) in acetonitrile (20 mL) was added 3-diethoxyphosphoryloxy-1,2,3-benzotriazin-4(3H)-one (DEPBT, 632 mg, 2.11 mmol) and triethylamine (600 μL, 4.4 mmol). The mixture was stirred for 4 d at room temperature. The red precipitate was collected by filtration and washed with acetonitrile to give N-(4-amino-3-nitrophenyl)-2-(1H-imidazol-1-yl)acetamide (430 mg, 88% yield), 98% pure. A solution of N-(4-amino-3-nitrophenyl)-2-(1H-imidazol-1-yl)acetamide (430 mg, 1.65 mmol) in ethanol (20 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (100 mg, 0.09 mmol) at room temperature overnight. The mixture was filtered, giving a blue solution. Removal of the solvent under reduced pressure gave N-(3,4-diaminophenyl)-2-(1H-imidazol-1-yl)acetamide (413 mg) as a blue semi-solid.

Workup

  1. filtrationThe red precipitate was collected by filtration
  2. washwashed with acetonitrile

Sources & evidence

ORD record
ord-199581a9278b4f97a65b56a79ae1ada1
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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