Hydrogen Bromide → 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole

HRID 1181631Notes

Reaction equation

HRID 1181631 reaction equation
BrBr.C([NH:6][CH:7]1[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]1)(=O)C.[NH2:14][C:15]([NH2:17])=[S:16].Br>O>[NH2:14][C:15]1[S:16][C:9]2[CH2:8][CH:7]([NH2:6])[CH2:12][CH2:11][C:10]=2[N:17]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 24408Bromine2×HCID 538565N-(4-Oxocyclohexyl)acetamideHCID 2723790Thiourea

Product 1

HCID 103297212,6-Diamino-4,5,6,7-tetrahydrobenzothiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Bromine (112 g) was added dropwise to a solution of 4-acetamidocyclohexanone (100 g) in 500 ml water at room temperature. The mixture was warmed to approximately 45° C. and maintained at this temperature until the bromine colour had been lost. To this, thiourea (125 g) was added, and the mixture was heated to approximately 80° C. To this, aqueous hydrobromic acid (100 ml) was added, and the contents of the reaction vessel were refluxed. The contents were then cooled to approximately 10° C., and neutralized with caustic lye solution. The product, 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole, was isolated by filtration, and washed with chilled water and dried. The product was off-white in colour, and the yield was approximately 60 g in weight.

Workup

  1. temperaturethe mixture was heated to approximately 80° C
  2. temperaturethe contents of the reaction vessel were refluxed
  3. temperatureThe contents were then cooled to approximately 10° C.

Sources & evidence

ORD record
ord-be3b1820b61f486ca35d73792e2e7a38
Source dataset
uspto-grants-2007_10
Patent number
US07285669B2

Reaction notes

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