Triethylamine → 1-(6-Chloro-2-methyl-phenyl)-3-ethyl-3,4,5,6-tetrahydro-pyrimidine-2(1h)-thione

HRID 1250899Notes

Reaction equation

HRID 1250899 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH3:14])=[C:6]([CH3:15])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23](Cl)(Cl)=[S:24]>C(Cl)(Cl)Cl.ClCCl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[C:23]2=[S:24])=[C:6]([CH3:15])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 18324822N'-(6-Chloro-2-methyl-phenyl)-N-ethyl-propane-1,3-diamine

Product 1

HCID 98168481-(6-Chloro-2-methyl-phenyl)-3-ethyl-3,4,5,6-tetrahydro-pyrimidine-2(1h)-thioneYield 59.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of the diamine of Step A (3.4 g) and triethylamine (4.0 mL) in dry chloroform (50 mL) was added thiophosgene (1.7 mL). After 20 minutes at ambient temperature, the reaction was quenched with water and extracted with dichloromethane. The extracts were combined, dried over sodium sulfate and concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with 11% ethyl acetate in hexane provided an orange solid which was triturated with diethyl ether to give the title product (2.4 g, 59.5%) as a white solid, m.p. 88-90° C.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil
  6. customabsorbed onto a column of Merck-60 flash silica gel
  7. washElution with 11% ethyl acetate in hexane
  8. customprovided an orange solid which
  9. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-93fb9725ceab48268052c3139f79032b
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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