Ethoxalyl chloride → HCID 10214869, compound

HRID 1241629Notes

Reaction equation

HRID 1241629 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[S:18])=[CH:12][CH:11]=1>ClCCl>[CH3:22][C:21]([CH3:24])([CH3:23])[CH2:20][N:19]1[C:2](=[O:8])[C:3](=[O:5])[N:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)[C:17]1=[S:18]

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 21936573HCID 21936573, compound

Product 1

HCID 10214869HCID 10214869, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.60 mL, 5.41 mmol) was added to a stirring solution of the above thiourea (1.00 g, 4.16 mmol) in dichloromethane (20 mL) and the resulting mixture was stirred overnight at room temperature. Concentration, trituration of the residue with diethyl ether, and recrystallization from boiling methanol afforded 0.77 g (62%) 1-(2,2-dimethyl-propyl)-3-(4-fluoro-phenyl)-2-thioxo-imidazolidine-4,5-dione as an orange-yellow solid: mp 165.2–166.3° C.; 1H NMR (DMSO-d6): δ 7.40 (m, 4H), 3.73 (s, 2H), 0.98 (s, 9H); IR (KBr): 3500, 2980, 1770 cm1; MS (m/z) 294 (M+).

Workup

  1. concentrationConcentration, trituration of the residue
  2. customwith diethyl ether, and recrystallization

Sources & evidence

ORD record
ord-7df462e50f13448bab165ba5fd6131d7
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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