Triethylamine → HCID 2252731, compound

HRID 720481Notes

Reaction equation

HRID 720481 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([N:8]=[C:9]=[S:10])[CH:7]=1.Cl.CN.[CH2:15]([N:17](CC)CC)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([NH:8][C:9]([NH:17][CH3:15])=[S:10])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 6364545Methylamine hydrochloride

Product 1

HCID 2252731HCID 2252731, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Chloro-2-methylphenyl isothiocyanate (36.6 g; 0.2 mol) was added to the solution of methylamine hydrochloride (26.8 g; 0.4 mol) in chloroform (300 mL). Triethylamine (65 mL; 0.47 mol) was added dropwise while stirring at ambient temperature. The mixture was stirred for 18 hours. The solvent was evaporated. The residue was treated with ethyl acetate (800 mL) and water (400 mL). The organic phase was separated, washed with water (2×300 mL), dried over magnesium sulfate and evaporated to dryness to give 41.6 g of N-(5-chloro-2-methylphenyl)-N′-methylthiourea, m.p. 139–140° C.

Workup

  1. stirringThe mixture was stirred for 18 hours
  2. customThe solvent was evaporated
  3. additionThe residue was treated with ethyl acetate (800 mL) and water (400 mL)
  4. customThe organic phase was separated
  5. washwashed with water (2×300 mL)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0621c9e6cbd5400180027e6d5316095c
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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