4-Methylbenzoyl Chloride → HCID 138962834, compound

HRID 1824017Notes

Reaction equation

HRID 1824017 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[CH3:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1>[OH-].[Na+].CCOCC>[CH3:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:10][C:8](=[NH:9])[S:7][CH3:6])=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 138962834HCID 138962834, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-methyl-2-thiopseudourea sulfate (6.9 g, 0.025 mol) in 30 ml of sodium hydroxide (4%) was added a solution of 4-methylbenzoyl chloride (3.4 g, 0.022 mol) in ether (10 ml) at room temperature. The reaction mixture was stirred overnight and the precipitated solid was filtered, washed with water, later hexanes and dried under high vacuum. N-(4-methylbenzoyl)-S-methylisothiourea: yield 4.60 g (quantitative); purity 98% (HPLC); 1H-NMR (CD3OD) δ 2.4 (s, 3H, CH3), 2.6 (s, 3H, SMe), 7.2 (d, 2H, ArH), 8.1 (d, 2H, ArH).

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with water, later hexanes
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-1e2a4d9a81974114acb5f92a9bf01619
Source dataset
uspto-grants-2006_05
Patent number
US07041702B1

Reaction notes

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