Benzo(d)thiazol-2-amine → 1-(1,3-Benzothiazol-2-yl)-3-[2-(cyclohexen-1-yl)ethyl]thiourea

HRID 233680Notes

Reaction equation

HRID 233680 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[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1.C(OCC)(=O)C>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[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 8706Benzo(d)thiazol-2-amineHCID 8857Ethyl AcetateHCID 27358811-(2-Isothiocyanatoethyl)cyclohex-1-ene

Product 1

HCID 30055431-(1,3-Benzothiazol-2-yl)-3-[2-(cyclohexen-1-yl)ethyl]thioureaYield 40.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(1-cyclohexenyl)ethyl isothiocyanate (3.3 g, 20 mmol) and 2-aminobenzothiazole (3.0 g, 20 mmol) in N,N-dimethylformamide (50 mL) was heated at 100° C. for 17.5 h. The reaction was cooled to room temperature, poured into ethyl acetate, washed with water, 1N aqueous HCl, water, saturated sodium bicarbonate, and brine. The organic layer was concentrated and the residue recrystallized from ethyl acetate to provide 2.57 g (40%) of the title product:

Workup

  1. washwashed with water, 1N aqueous HCl, water, saturated sodium bicarbonate, and brine
  2. concentrationThe organic layer was concentrated
  3. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e7fb97ef7fde4c88babbf60830d864c5
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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