Thiourea → 4-cyclohexyl-1,3-thiazol-2-amine

HRID 2059049Notes

Reaction equation

HRID 2059049 reaction equation
[CH:1]1([CH:7]([C:9](C(Br)C2CCCCC2)=O)Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:19][C:20]([NH2:22])=[S:21]>C(O)C>[NH2:22][C:20]1[S:21][CH:9]=[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:19]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86738298HCID 86738298, compound

Product 1

HCID 3469304-cyclohexyl-1,3-thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclohexylbromomethylketone (49 g., 0.24 mole) was added to a slurry of thiourea (20.1 g., 0.26 mole) in 250 ml. of ethanol and the mixture heated to reflux. The resulting solution was refluxed for 2 hours, cooled to room temperature and evaporated in vacuo to an oil. The oil was taken up in 100 ml. of water, the solution made basic with concentrated ammonium hydroxide and crude product recovered in two crops by filtration. Crude product was recrystallized from cyclohexane to yield purified 2-amino-4-cyclohexylthiazole (20.4 g.; m.p. 141°-143° C.).

Workup

  1. temperatureThe resulting solution was refluxed for 2 hours
  2. customevaporated in vacuo to an oil
  3. filtrationrecovered in two crops by filtration
  4. customCrude product was recrystallized from cyclohexane
  5. customto yield
  6. custompurified 2-amino-4-cyclohexylthiazole (20.4 g.; m.p. 141°-143° C.)

Sources & evidence

ORD record
ord-e0a35c62588544729d99d8f8de5e3663
Source dataset
uspto-grants-1982_03
Patent number
US04321372

Reaction notes

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