2-Amino-4,5,6,7-tetrahydrobenzothiazole → HCID 57486206, compound

HRID 250005Notes

Reaction equation

HRID 250005 reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[NH2:10].[N:11]1([C:16](N2C=CN=C2)=[S:17])[CH:15]=[CH:14][N:13]=[CH:12]1>C(#N)C>[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[NH:10][C:16]([N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)=[S:17]

Participants

4

Reactant 2

HCID 180462-Amino-4,5,6,7-tetrahydrobenzothiazoleHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 57486206HCID 57486206, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine (0.5 g, 3.24 mmol) in acetonitrile (20 mL) was added di(1H-imidazol-1-yl)methanethione (0.58 g, 3.24 mmol). The reaction was stirred at 50° C. for 4 hours. The reaction was cooled and concentrated to yield crude product. The crude material was purified via flash chromatography (50-100% ethyl acetate-hexane) to yield N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide (0.60 g, 2.27 mmol, 70.0% yield) as a white powder.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customto yield crude product
  4. customThe crude material was purified via flash chromatography (50-100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-de0db8744a7246fe82a8adbc3d82a098
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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