Sodium Iodide → HCID 57617817, compound

HRID 2421839Notes

Reaction equation

HRID 2421839 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[S:15][CH2:16][CH2:17]Cl)[C:5]([NH:7][CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6].[I-].[Na+]>CC(=O)CC>[CH2:8]([NH:7][C:5]([C:4]1[CH:12]=[CH:13][C:14]2[S:15][CH2:16][CH2:17][NH:1][C:2]=2[CH:3]=1)=[O:6])[CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 67241888HCID 67241888, compound

Product 1

HCID 57617817HCID 57617817, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-amino-4-(2-chloroethylthio)-N-isobutylbenzamide (2.386 g, 8.32 mmol) in 2-butanone (150 ml) was added sodium iodide (1.247 g, 8.32 mmol). The reaction was heated to 70° C. and stirred for 24 hours. TLC analysis of the reaction mixture indicated consumption of starting material. The reaction mixture was concentrated in vacuo and purified by flash column chromatography [gradient elution (hexanes with 5-50% EtOAc)] to provide N-isobutyl-3,4-dihydro-2H-benzo[b][1,4]-thiazine-6-carboxamide (1.61 g, 6.43 mmol) as an off white solid. The total overall yield for steps 2-5 was 77%. LCMS (+ESI) m/z=523.34 [2M+Na]+.

Workup

  1. customconsumption of starting material
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash column chromatography [gradient elution (hexanes with 5-50% EtOAc)]

Sources & evidence

ORD record
ord-0a53ee228fb04ba2b71c0fd49c834ecb
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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