Sodium Acetate → 2-Amino-5-methyl-4,5,6-trihydrobenzothiazol-7-one

HRID 879256Notes

Reaction equation

HRID 879256 reaction equation
Br[CH:2]1[C:7](=[O:8])[CH2:6][CH:5]([CH3:9])[CH2:4][C:3]1=O.C([O-])(=O)C.[Na+].[NH2:16][C:17]([NH2:19])=[S:18]>C(O)(=O)C>[NH2:19][C:17]1[S:18][C:2]2[C:7](=[O:8])[CH2:6][CH:5]([CH3:9])[CH2:4][C:3]=2[N:16]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 669327192-Bromo-5-methylcyclohexane-1,3-dione

Product 1

HCID 27565102-Amino-5-methyl-4,5,6-trihydrobenzothiazol-7-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 24 in acetic acid (540 mL) was added sodium acetate (44.3 g, 540 mmol) and thiourea (28.8 g, 378 mmol). The reaction mixture was stirred with a mechanical stirrer at 100° C. for 3 h. The reaction mixture was partially concentrated in vacuo. EtOAc was added (500 mL). The mixture was made basic with 1 M NaOH, and the layers were separated. The aqueous layer was extracted with EtOAc (2×300 mL). The combined organic layers were dried, filtered, and concentrated in vacuo to give 49.3 g of 25, which was taken on without further purification. LCMS-ESI+: calc'd for C8H11N2OS: 183.1 (M+H+); Found: 183.1 (M+H+).

Workup

  1. concentrationThe reaction mixture was partially concentrated in vacuo
  2. additionEtOAc was added (500 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc (2×300 mL)
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-928c7de9f3c6416ab9a1e10bfda5660e
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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