Triethylamine → HCID 10431373, compound

HRID 487562Notes

Reaction equation

HRID 487562 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]([NH2:15])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:5].Cl.C(N(CC)CC)C.[CH:24]([C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[S:35])=[CH:29][CH:28]=1)([CH3:26])[CH3:25]>CCOCC>[CH:24]([C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:15][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)=[S:35])=[CH:29][CH:28]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1451944-Isopropylphenyl isothiocyanateHCID 272392652031-05-7

Product 1

HCID 10431373HCID 10431373, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

DL-4-Chlorophenylalanine ethyl ester hydrochloride(5 g, 18.9 mmol) was converted to the free base using triethylamine. A solution of the free base in 75 mL ether was added to a solution of 4-isopropylphenylisothiocyanate in 150 mL ether, cooled on an ice-salt bath. The temperature was maintained at about 0° C. during addition. The reaction was stirred for four and one-half hours, at which time the reaction temperature was 12° C.. The reaction mixture was filtered, the filtrate concentrated, and the resulting foamy residue triturated with petroleum ether while cooling on ice. This resulted in 6.1 g (15.1 mmol, 80%) N-(4-isopropylphenyl)-N'-[2-(4-chlorophenyl)-1-(ethoxycarbonyl)ethyl]thiourea, mp 73°-75° C.

Workup

  1. temperaturecooled on an ice-salt bath
  2. customwas 12° C.
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated
  5. customthe resulting foamy residue triturated with petroleum ether
  6. temperaturewhile cooling on ice

Sources & evidence

ORD record
ord-45e936e3dd4246ffb4aa3b90f03e3912
Source dataset
uspto-grants-1994_03
Patent number
US05296486

Reaction notes

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