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

HRID 1835617Notes

Reaction equation

HRID 1835617 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][C:9](=O)[CH2:8][CH2:7][C:5]=2[N:6]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:18].[Na+].Cl>CO>[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([NH2:18])[CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 98774852-Amino-4,7-dihydro-1,3-benzothiazol-6(5H)-one

Product 1

HCID 103297212,6-Diamino-4,5,6,7-tetrahydrobenzothiazoleYield 70.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-amino-6-oxo-4,5,6,7-tetrahydro-1,3-benzothiazole (2.0 g, 12 mmol), ammonium acetate (9.2 g, 120 mmol) and sodium cyanoborohydride (0.53 g, 8.4 mmol) in 40 mL of methanol was stirred under nitrogen at ambient temperature for 48 hours. Concentrated HCl was added and methanol was removed in vacuo. The residue was mixed with water and solution was made alkaline with NaOH. White precipitate was removed by filtration, washed with water and dried to give 1.0 g of the title compound. The structure of the product was confirmed by NMR.

Workup

  1. custommethanol was removed in vacuo
  2. additionThe residue was mixed with water and solution
  3. customWhite precipitate was removed by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-877989e0858c4683ae07c82b774c755b
Source dataset
uspto-grants-2004_08
Patent number
US06770761B2

Reaction notes

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