Methane → 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole, (S)-

HRID 418348Notes

Reaction equation

HRID 418348 reaction equation
O.O.O.C(C(C(C(O)=O)O)O)(O)=O.[S:14]1[C:18]2[CH2:19][C@@H:20]([NH2:23])[CH2:21][CH2:22][C:17]=2[N:16]=[C:15]1[NH2:24].C>Cl>[S:14]1[C:18]2[CH2:19][C@@H:20]([NH2:23])[CH2:21][CH2:22][C:17]=2[N:16]=[C:15]1[NH2:24]

Participants

4

Reactant 2

HCID 297MethaneHCID 86639093(S)-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine tartrate trihydrate

Product 1

HCID 115211532,6-Diamino-4,5,6,7-tetrahydrobenzothiazole, (S)-Yield 69.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

Dissolved (S)-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine tartrate trihydrate (80.0 g, 214.25 mmol) in 50 mL of 2 M HCl, giving a dark gray solution. To this was added decolorizing charcoal (20 g). The mixture stirred for 30 min. Filtered the mixture and washed with 20 mL H2O. The filtrate was heated at 50° C. with stirring. Solid NaOH was added slowly until the pH was basic. Cooling to room temperature followed by refrigeration for 2 h gave a white ppt. Filtered the white ppt and placed it in a vacuum drying oven overnight at 40° C. Collected the material giving 25.19 g of (S)-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine. 1H NMR showed pure freebase.

Workup

  1. customgiving a dark gray solution
  2. additionTo this was added
  3. filtrationFiltered the mixture
  4. washwashed with 20 mL H2O
  5. stirringwith stirring
  6. additionSolid NaOH was added slowly until the pH
  7. temperatureCooling to room temperature
  8. waitfollowed by refrigeration for 2 h
  9. customgave a white ppt
  10. filtrationFiltered the white ppt
  11. customdrying oven overnight at 40° C
  12. customCollected the material

Sources & evidence

ORD record
ord-ddf565093c8a4df88b81e12466f426e0
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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