1-(2-Aminoethyl)-3-phenylthiourea → HCID 21272432, compound

HRID 1981553Notes

Reaction equation

HRID 1981553 reaction equation
[O:1]1[CH2:13][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[N:12].[NH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[S:19]>C(O)(C)C>[OH2:1].[C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH:2]([OH:1])[CH2:13][NH:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[S:19])#[N:12]

Participants

4

Reactant 2

HCID 21434541-(2-Aminoethyl)-3-phenylthioureaHCID 126196712-(Oxiran-2-ylmethoxy)benzonitrile

Product 1

HCID 21272432HCID 21272432, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution was prepared of 1.75 g (0.01 mole) of 2,3-epoxy-1-(2-cyanophenoxy)propane, 7, in 50 ml of isopropyl alcohol, assisted by gentle warming and sonication. To this was next added 2.95 g (0.01 mole) of 12 all at once. The solution was refluxed for one hour then stirred overnight at room temperature. The solution was concentrated in vacuo to 5.6 of gum, which was chromatographed over 150 g of silica gel using 10% CH3OH/CHCl3 (saturated with NH3) and taking 10 ml fractions. Fractions 12-41 gave 1.8 g of a foam which was found to be nonhomogeneous. This material was rechromatographed over 200 g of silica gel using the same solvent system as before and taking 10 ml cuts. Fractions 12-30 gave 400 mg (12%) of yellow sticky 13, m.p. 41°-47° C. Rf =0.64 (silica gel GF, 10% CH 3 OH/CHCl3 (NH3)). Mass spectrum, m/e 370 (M+); liquid chromatography showed 98% pure. Analysis satisfactory for C19H22N4O2S.1.6H2O.

Workup

  1. temperatureby gentle warming
  2. customsonication
  3. temperatureThe solution was refluxed for one hour
  4. concentrationThe solution was concentrated in vacuo to 5.6 of gum, which
  5. customwas chromatographed over 150 g of silica gel using 10% CH3OH/CHCl3 (saturated with NH3)

Sources & evidence

ORD record
ord-2c0bee1182e643ca9c1bc5dc2e9f0d79
Source dataset
uspto-grants-1986_06
Patent number
US04593039

Reaction notes

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