Hydrochloric Acid → 2-Amino-4,5,6,7-tetrahydrobenzothiazole

HRID 2058858Notes

Reaction equation

HRID 2058858 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[NH2:9][C:10]([NH2:12])=[S:11].Cl>O>[NH2:12][C:10]1[S:11][C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 132032-ChlorocyclohexanoneHCID 2723790Thiourea

Product 1

HCID 180462-Amino-4,5,6,7-tetrahydrobenzothiazoleYield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-chlorocyclohexanone (6.63 grams; 0.05 mol) and thiourea (3.81 grams; 0.05 mol) were charged into a glass reaction vessel and heated overnight on a steam bath. The product was poured in water (100 ml.) and was acidified with hydrochloric acid. The unreacted ketone was extracted from the reaction mixture by using ethanol (25 ml.) five times and the aqueous portion withdrawn and adjusted to a pH of 9 with aqueous sodium hydroxide. The product was then extracted with ethanol, dried over anhydrous magnesium sulfate and evaporated on a rotary evaporator resulting in 6.3 grams of desired product having a melting point of 84°-87° C. The structure of the product was confirmed by infrared spectroscopy.

Workup

  1. temperatureheated overnight on a steam bath
  2. extractionThe unreacted ketone was extracted from the reaction mixture
  3. customthe aqueous portion withdrawn
  4. extractionThe product was then extracted with ethanol
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-c67617f2a21341aabe9ee37dffce052f
Source dataset
uspto-grants-1982_03
Patent number
US04319914

Reaction notes

Loading…