Ethanethiol → HCID 53629164, compound

HRID 1924252Notes

Reaction equation

HRID 1924252 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][N:6]([CH3:11])[C:7]=1[C:8](O)=[O:9])#[N:2].[CH2:12]([SH:14])[CH3:13].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([C:3]1[N:4]=[CH:5][N:6]([CH3:11])[C:7]=1[C:8](=[O:9])[S:14][CH2:12][CH3:13])#[N:2]

Participants

6

Reactant 3

HCID 6343Ethanethiol2×HCID 10868DicyclohexylcarbodiimideHCID 450820154-Cyano-1-methyl-1H-imidazole-5-carboxylic acid

Product 1

HCID 53629164HCID 53629164, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 1 l, three-necked flask fitted with a magnetic stirrer and a reflux condenser under inert atmosphere, 4-cyano-1-methyl-1H-imidazole-5-carboxylic acid x84 (24.5 g, 0.162 mol) and CH2Cl2 (500 ml) are stirred at room temperature. To this suspension, ethanethiol (13.2 ml, 0.178 mol) and DMAP (1.98 g, 0.016 mol) are added, followed by DCC (36.77 g, 0.178 mol) in two portions. The temperature rises to 35° C. and the mixture is stirred at room temperature for 16 h. Ethanethiol (0.0324 mol) is further added and stirring is continued overnight. The mixture is filtered and the solvent is evaporated. The residue is purified by chromatography on silicagel (Hexane/AcOEt:6/4 (v/v)) to give 29.5 g of S-ethyl 4-cyano-1-methyl-1H-imidazole-5-carbothioate x85.

Workup

  1. customrises to 35° C.
  2. stirringthe mixture is stirred at room temperature for 16 h
  3. stirringstirring
  4. filtrationThe mixture is filtered
  5. customthe solvent is evaporated
  6. customThe residue is purified by chromatography on silicagel (Hexane/AcOEt:6/4 (v/v))

Sources & evidence

ORD record
ord-6dbf05ecbdbc4d6c830d65be9243e230
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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