Toluene → N-(2-Amino-3-methoxyphenyl)-N'-(4-methyl-3-thienyl)thiourea

HRID 2250493Notes

Reaction equation

HRID 2250493 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:10])=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.[CH3:11][C:12]1[C:13]([N:17]=[C:18]=[S:19])=[CH:14][S:15][CH:16]=1.C1(C)C=CC=CC=1.C(OCC)(=O)C>C1COCC1>[NH2:10][C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:9][C:18]([NH:17][C:13]1[C:12]([CH3:11])=[CH:16][S:15][CH:14]=1)=[S:19]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 1842683-Methoxybenzene-1,2-diamineHCID 221398273-Isothiocyanato-4-methylthiophene

Product 1

HCID 22139816N-(2-Amino-3-methoxyphenyl)-N'-(4-methyl-3-thienyl)thiourea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

is obtained analogously to the procedure described in example 25 a) from 3-methoxy-1,2-diaminobenzene and 4-methyl-3-thienyl isothiocyanate in anhydrous THF, followed by medium-pressure chromatography on silica gel using a mixture of 1 part of toluene and 1 part of ethyl acetate. Crystalline solid, m.p.: 148-153° C. Solidification of the melt and next m.p. at 260° C.

Workup

  1. customis obtained analogously to the procedure
  2. customat 260° C.

Sources & evidence

ORD record
ord-1951bb654f3944619e3acc68147333ce
Source dataset
uspto-grants-2008_01
Patent number
US07317033B2

Reaction notes

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