Ethoxalyl chloride → 1-(4-Dimethylamino-phenyl)-3-(2,2-dimethyl-propyl)-2-thioxo-imidazolidine-4,5-dione Hydrochloride

HRID 1241620Notes

Reaction equation

HRID 1241620 reaction equation
[Cl:1][C:2](=[O:8])[C:3]([O:5]CC)=O.[CH3:9][N:10]([CH3:26])[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[S:19])=[CH:13][CH:12]=1>ClCCl>[ClH:1].[CH3:26][N:10]([CH3:9])[C:11]1[CH:12]=[CH:13][C:14]([N:17]2[C:2](=[O:8])[C:3](=[O:5])[N:20]([CH2:21][C:22]([CH3:23])([CH3:25])[CH3:24])[C:18]2=[S:19])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 21936574N-[4-(dimethylamino)phenyl]-N'-(2,2-dimethylpropyl)-thiourea

Product 1

HCID 102370511-(4-Dimethylamino-phenyl)-3-(2,2-dimethyl-propyl)-2-thioxo-imidazolidine-4,5-dione HydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (3.4 mL, 30 mmol) was added dropwise to a stirring solution of N-[4-(dimethylamino)phenyl]-N′-(2,2-dimethylpropyl)-thiourea (3.98 g, 15 mmol) in dichloromethane (100 mL) and the resulting mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was treated with ether (100 mL) and the mixture was stirred for one hour. The solid was collected by filtration, washed with fresh ether and dried to give 5.3 g (100%) of the title compound: mp. 244–246° C.; 1H NMR (DMSO-d6): δ7.28 (d, 2H), 7.20 (br s, 2H), 3.74 (s, 2H), 3.02 (s, 6H), and 0.98 ppm (s, 9H); IR (KBr) 3640, 3080, 2350, 1775 cm−1; MS (m/z) 319 (M+).

Workup

  1. customThe solvent was evaporated
  2. additionThe residue was treated with ether (100 mL)
  3. stirringthe mixture was stirred for one hour
  4. filtrationThe solid was collected by filtration
  5. washwashed with fresh ether
  6. customdried

Sources & evidence

ORD record
ord-7dce98350c764426a0bdce65be9996e0
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

Loading…