2-Methyl-2-thiopseudourea sulfate → HCID 140476686, compound

HRID 1710444Notes

Reaction equation

HRID 1710444 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:30][CH3:31])=[C:16]([CH2:18][CH2:19][C:20]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:21]=2[C:22](Cl)=[O:23])[CH:17]=1>[OH-].[Na+].C(OCC)C.O>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:30][CH3:31])=[C:16]([CH2:18][CH2:19][C:20]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([NH:10][C:8](=[NH:9])[S:7][CH3:6])=[O:23])[CH:17]=1

Participants

6

Reactant 2

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 59700988HCID 59700988, compound

Product 1

HCID 140476686HCID 140476686, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-methyl-2-thiopseudourea sulfate (1.6 g, 5.75 mmol, 2.5 equiv) in 1N NaOH (10 mL) was cooled to 0° C. To this solution was added dropwise a solution of 2-[2-(5-bromo-2-methoxyphenyl)-ethyl]-3-fluoro-benzoyl chloride (2.3 mmol, 1 equiv) in diethyl ether (4 mL). The solution-was allowed to stir for 3.5 hr and then diluted with H2O. The aqueous solution was extracted with dichloromethane and the combined organic phases were dried over Na2SO4, filtered, and concentrated to give 1-{2-[2-(5-bromo-2-methoxyphenyl)-ethyl]-3-fluorobenzoyl}-2-methylisothiourea in quantitative yield. The crude product was used without further purification. 1H NMR (300 MHz, CDCl3) δ 7.72 (d, J=7.2 Hz, 1H), 7.07-7.30 (m, 4H), 6.68 (d, J=8.1 Hz, 1H), 3.73 (s, 3H), 3.27-3.33 (m, 2H), 2.84-2.90 (m, 2H), and 2.52 (s, 3H).

Workup

  1. extractionThe aqueous solution was extracted with dichloromethane
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3b06befb40da4cb3a6dbe871b50892d5
Source dataset
uspto-grants-2010_09
Patent number
US07790719B2

Reaction notes

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