Bromine → N6-propyl-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine dihydrobromide

HRID 1942415Notes

Reaction equation

HRID 1942415 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:6]2)OCC1.[Br:15]Br.[NH2:17][C:18]([NH2:20])=[S:19]>Br>[BrH:15].[BrH:15].[CH2:12]([NH:11][CH:8]1[CH2:9][CH2:10][C:5]2[N:17]=[C:18]([NH2:20])[S:19][C:6]=2[CH2:7]1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 24408BromineHCID 2723790ThioureaHCID 118200814-n-Propylamino-cyclohexanone-ethyleneketal

Product 1

HCID 86651296N6-propyl-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine dihydrobromide

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 12.0 g (60 mmol) (1,4-dioxa-spiro[4.5]dec-8-yl)-propyl-amine in 120 mL concentrated aqueous hydrobromic acid is stirred for 15 minutes at room temperature and then 3.12 mL (60 mmol) bromine are added. After further stirring for 15 minutes 4.56 g (60 mmol) of thiourea is added. The resulting solution is stirred for another at room temperature until a white precipitation can be observed. Afterwards the mixture is heated for 2 hours at 90° C. The clear reaction mixture is then concentrated under vacuum. The solid residue is suspended in ethanol, heated to reflux and filtrated after cooling to room temperature. The resulting residue is dried under high vacuum.

Workup

  1. additionis added
  2. customuntil a white precipitation
  3. temperatureAfterwards the mixture is heated for 2 hours at 90° C
  4. concentrationThe clear reaction mixture is then concentrated under vacuum
  5. temperatureheated
  6. temperatureto reflux
  7. filtrationfiltrated
  8. temperatureafter cooling to room temperature
  9. customThe resulting residue is dried under high vacuum

Sources & evidence

ORD record
ord-f9344b8bca1b4003be51e16f5b79b1b3
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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