2-Amino-4,5,6,7-tetrahydrobenzothiazole → HCID 19703901, compound

HRID 233704

Reaction equation

HRID 233704 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 19703901HCID 19703901, compoundYield 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-d5c227c25b4b45b1b6cd865fee535c41
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Linked notes

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