2-[(1H-Imidazol-2-yl)methyl]aniline → 1-[2-(2-Imidazolylmethyl)-phenylthiocarbamoyl]-4-ethoxycarbonylpiperazine

HRID 1462335Notes

Reaction equation

HRID 1462335 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][C:5]1[NH:6][CH:7]=[CH:8][N:9]=1.[CH2:14]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25](Cl)=[S:26])[CH2:21][CH2:20]1)=[O:18])[CH3:15]>O1CCCC1.C(N(CC)CC)C.C(Cl)Cl>[NH:9]1[CH:8]=[CH:7][N:6]=[C:5]1[CH2:4][C:3]1[CH:10]=[CH:11][CH:12]=[CH:13][C:2]=1[NH:1][C:25]([N:22]1[CH2:23][CH2:24][N:19]([C:17]([O:16][CH2:14][CH3:15])=[O:18])[CH2:20][CH2:21]1)=[S:26]

Participants

6

Reactant 2

HCID 133449032-[(1H-Imidazol-2-yl)methyl]anilineHCID 133449264-Ethoxycarbonyl-1-piperazinylthiocarbonyl chloride

Product 1

HCID 204033221-[2-(2-Imidazolylmethyl)-phenylthiocarbamoyl]-4-ethoxycarbonylpiperazine

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 3.8 g of 2-(2-aminobenzyl)imidazole in 38 ml of tetrahydrofuran and 3.23 ml of triethylamine was added dropwise a solution of 5.5 g of 4-ethoxycarbonyl-1-piperazinyl-thiocarbonyl chloride in 10 ml of methylene chloride at room temperature. The mixture was stirred for 1 week and the suspension filtered. The filtrate was washed with first 10% aqueous potassium carbonate, then with water, dried and evaporated to dryness to give amorphous 1-[2-(2-imidazolylmethyl)phenylthiocarbamoyl]-4-ethoxycarbonylpiperazine, characterized by NMR.

Workup

  1. filtrationthe suspension filtered
  2. washThe filtrate was washed with first 10% aqueous potassium carbonate
  3. dry with materialwith water, dried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-ee123d4837ea4ad3ae65b98c07d1f980
Source dataset
uspto-grants-1984_07
Patent number
US04460508

Reaction notes

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