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

HRID 1468696
Notes
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Reaction equation

HRID 1468696 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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.

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-5a35312db4704ff4bf19d9e36ce8f81b
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09006229B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes