2-Amino-4,5,6,7-tetrahydrobenzothiazole → N-[2-(1-cyclohexenyl)ethyl]-N'-[4,5,6,7-tetrahydrobenzothiazolyl]thiourea

HRID 861598Notes

Reaction equation

HRID 861598 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]=[C:10]=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[NH2:12][C:13]1[S:14][C:15]2[CH2:21][CH2:20][CH2:19][CH2:18][C:16]=2[N:17]=1>CN(C)C=O>[C:1]1([CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]2[S:14][C:15]3[CH2:21][CH2:20][CH2:19][CH2:18][C:16]=3[N:17]=2)=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 180462-Amino-4,5,6,7-tetrahydrobenzothiazoleHCID 27358811-(2-Isothiocyanatoethyl)cyclohex-1-ene

Product 1

HCID 19703901N-[2-(1-cyclohexenyl)ethyl]-N'-[4,5,6,7-tetrahydrobenzothiazolyl]thioureaYield 13.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(1-cyclohexenyl)ethyl isothiocyanate (1.67 g, 10 mmol) and 2-amino-4,5,6,7-tetrahydrobenzothiazole (1.54 g, 10 mmol) in N,N-dimethylformamide (100 mL) was heated at 100° C. for 120 h. The reaction was cooled to room temperature, the solvent removed under reduced pressure, the residue taken up in ethyl acetate and washed with 1N HCl. The organic layer was concentrated and the residue recrystallized from ethyl acetate-hexanes to provide 426 mg (13%) of the titled product:

Workup

  1. customthe solvent removed under reduced pressure
  2. washwashed with 1N HCl
  3. concentrationThe organic layer was concentrated
  4. customthe residue recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-dd6615da842147c2b4013eaf07a54769
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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