Triethylamine → N-(5-chloro-2-methylphenyl)-N'-(2-propynyl)thiourea

HRID 720486Notes

Reaction equation

HRID 720486 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.[CH2:13]([NH2:16])[C:14]#[CH:15].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([NH:8][C:9]([NH:16][CH2:13][C:14]#[CH:15])=[S:10])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 11205720Prop-2-ynylamine hydrochloride

Product 1

HCID 21893722N-(5-chloro-2-methylphenyl)-N'-(2-propynyl)thioureaYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chloro-2-methylphenyl isothiocyanate (18.3 g; 0.1 mol) was added dropwise to the mixture of 2-propynylamine hydrochloride (9.2 g, 0.1 mol) and triethyl amine (20 mL) in methylene chloride (200 mL). The mixture was stirred for 18 hours at ambient temperature. The mixture was evaporated to dryness. The residue was stirred in water (200 mL) for 1 hour then filtered. The solid was dissolved in ethyl acetate (300 mL) and washed with 1N hydrochloric acid (2×200 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness to give 16.8 g of N-(5-chloro-2-methylphenyl)-N′-(2-propynyl)thiourea.

Workup

  1. customThe mixture was evaporated to dryness
  2. stirringThe residue was stirred in water (200 mL) for 1 hour
  3. filtrationthen filtered
  4. dissolutionThe solid was dissolved in ethyl acetate (300 mL)
  5. washwashed with 1N hydrochloric acid (2×200 mL)
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d06104a7d2754cc8a51f79b224907719
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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