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

HRID 861578Notes

Reaction equation

HRID 861578 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-3ec80519de044525808fe85391282a7f
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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