Butanal → HCID 13670709, compound

HRID 569103Notes

Reaction equation

HRID 569103 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([NH2:11])[CH2:8][CH2:7][C:5]=2[N:6]=1.[CH:12](=O)[CH2:13][CH2:14][CH3:15].[BH4-].[Na+].[ClH:19]>CN(C)C=O.O>[ClH:19].[ClH:19].[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 261ButanalHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 103297212,6-Diamino-4,5,6,7-tetrahydrobenzothiazole

Product 1

HCID 13670709HCID 13670709, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3.4 g (0.02 Mol) of 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole in 34 ml of dimethylformamide are added 1.8 g (0.022 Mol) of n-butanal and the mixture is heated to 50° C. for 1 hour. After cooling, the reaction solution is mixed with 0.8 g (0.02 Mol) of sodium borohydride and heated to 50° C. for 30 minutes. The solvent is largely eliminated in vacuo. Whilst cooling with ice, the residue is mixed with 20 ml of water and 2N hydrochloric acid until a pH of 1 is obtained. The aqueous solution is extracted with ethylacetate and the organic phase discarded. The aqueous phase is mixed with potassium carbonate until an alkaline reaction is obtained and then extracted with ethyl acetate. The organic phase is dried and concentrated. The compound crystallizes out when ethereal hydrochloric acid is added.

Workup

  1. temperatureAfter cooling
  2. temperatureheated to 50° C. for 30 minutes
  3. temperatureWhilst cooling with ice
  4. customis obtained
  5. extractionThe aqueous solution is extracted with ethylacetate
  6. additionThe aqueous phase is mixed with potassium carbonate until an alkaline reaction
  7. customis obtained
  8. extractionextracted with ethyl acetate
  9. customThe organic phase is dried
  10. concentrationconcentrated
  11. customThe compound crystallizes out when ethereal hydrochloric acid
  12. additionis added

Sources & evidence

ORD record
ord-204f6f0783974c77b602d1ef04c48d1f
Source dataset
uspto-grants-1988_03
Patent number
US04731374

Reaction notes

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