Triethylamine → HCID 10561057, compound

HRID 745850Notes

Reaction equation

HRID 745850 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].C(N(CC)CC)C.[C:19]([N:21]=[CH:22]OCC)#[N:20].Cl.C(O)C>C(O)C>[C:19]([NH:21][CH:22]=[N:11][CH2:10][CH2:9][S:8][CH2:7][C:3]1[N:4]=[CH:5][NH:6][C:2]=1[CH3:1])#[N:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 9920370Methanimidic acid, N-cyano-, ethyl esterHCID 21887872Ethanol hydrochloride

Product 1

HCID 10561057HCID 10561057, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4.88 g of 2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethanamine (prepared according to British Pat. No. 1,338,169 which is hereby incorporated by reference,) in 75 ml of absolute ethanol, are added 5.55 ml of triethylamine. Then 1.96 g of ethyl N-cyano-formimidate in 15 ml of ethanol are added dropwise under stirring and at room temperature (prepared according to Huffman and Schaefer "J.Org.Chem.",28, 1816, 1963). Stirring is continued for 1 hour, after which are added 2.5 ml of 8N HCl/ethanol. A white solid is separated, which is subsequently crystallized in ethanol, filtered off and dried in a vacuum dessicator in the presence of phosphorus pentoxide and sodium hydroxide. 2.9 g of N-cyano-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]formamidine are obtained.

Workup

  1. custom(prepared according to Huffman and Schaefer "J.Org.Chem.",28, 1816, 1963)
  2. stirringStirring
  3. customA white solid is separated
  4. customwhich is subsequently crystallized in ethanol
  5. filtrationfiltered off
  6. dry with materialdried in a vacuum dessicator in the presence of phosphorus pentoxide and sodium hydroxide

Sources & evidence

ORD record
ord-4203c00b6f8c414d89b6142207332a99
Source dataset
uspto-grants-1986_07
Patent number
US04600780

Reaction notes

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