Triethylamine → 4-(2,4-dichlorophenyl)-5-methyl-2-[N-(dicyclopropylmethyl)-N-propylamino]thiazole

HRID 128696Notes

Reaction equation

HRID 128696 reaction equation
[CH:1]1([CH:4]([CH:12]2[CH2:14][CH2:13]2)[N:5]([CH2:9][CH2:10][CH3:11])[C:6]([NH2:8])=[S:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH:23]([CH3:34])[C:24]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33])=O>C(O)C>[Cl:33][C:27]1[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:26]=1[C:24]1[N:8]=[C:6]([N:5]([CH:4]([CH:1]2[CH2:3][CH2:2]2)[CH:12]2[CH2:13][CH2:14]2)[CH2:9][CH2:10][CH3:11])[S:7][C:23]=1[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109239912-Bromo-1-(2,4-dichlorophenyl)propan-1-one2×HCID 18967796N-(dicyclopropylmethyl)-N-propylthiourea2×

Product 1

HCID 193748924-(2,4-dichlorophenyl)-5-methyl-2-[N-(dicyclopropylmethyl)-N-propylamino]thiazoleYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 1 g of N-(dicyclopropylmethyl)-N-propylthiourea (Compound 88) dissolved in 25 ml of anhydrous ethanol, add 0.54 ml of triethylamine, then slowly 1 g of 2-bromo-1-(2,4-dichlorophenyl)-1-propanone (Compound 15). After two hours of heating under reflux of the ethanol, evaporate to dryness. Take up the residue in methylene chloride and wash with water until bromide ions have been removed completely. Dry the organic phase over anhydrous sodium sulphate and then evaporate to dryness. Purify the residue on a silica column, using a mixture of cyclohexane and ethyl acetate (20:1 V/V) as eluent, to obtain the expected product in the form of an oil.

Workup

  1. temperatureAfter two hours of heating
  2. customevaporate to dryness
  3. washwash with water until bromide ions
  4. customhave been removed completely
  5. dry with materialDry the organic phase over anhydrous sodium sulphate
  6. customevaporate to dryness
  7. customPurify the residue on a silica column
  8. additiona mixture of cyclohexane and ethyl acetate (20:1 V/V) as eluent

Sources & evidence

ORD record
ord-ba9a4d120cfa490e85c15c7a62715150
Source dataset
uspto-grants-1995_11
Patent number
US05464847

Reaction notes

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