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

HRID 901984Notes

Reaction equation

HRID 901984 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-fluorobenzoyl 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-e1d06ac4f6ff41c8ac9bab41d862b198
Source dataset
uspto-grants-2008_04
Patent number
US07365070B2

Reaction notes

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