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

HRID 2257783Notes

Reaction equation

HRID 2257783 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 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: IR (KBr, cm-1) 3169, 3031, 2931, 1580, 1258, 1198; 1H NMR (300 MHz, DMSO-d6) δ 11.41 (br s, 1H), 10.05 (br s, 1H), 5.43 (s, 1H), 3.58 (m, 2H), 2.6-1.9 (m, 10H), 1.7 (m, 4H), 1.5 (m, 4H); MS (FD) m/e 321 (M+); UV (EtOH) 298 nm (ε-12157), 257 nm (ε=6569), 201 nm (ε=12172). Anal. Calcd for C16H23N3S2 : C, 59.97 H, 7.21; N, 13.07. Found: C, 60.06; H, 6.95; N, 12.82.

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-c4b8cdb6d8244901b493c20577aa433d
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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