Methyl iodide → 7-Nitro-4-methyl-4H-benzo[1,4]thiazin-3-one

HRID 9721Notes

Reaction equation

HRID 9721 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][S:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:17]I>CN(C=O)C>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[N:8]([CH3:17])[C:9](=[O:12])[CH2:10][S:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3701217-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-one

Product 1

HCID 218777807-Nitro-4-methyl-4H-benzo[1,4]thiazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

7.3 g 7-Nitro-4H-benzo[1,4]thiazin-3-one was suspended in 65 ml DMF and treated in portions with 1.6 g of 55% sodium hydride. Stirring a room temperature was continued for 0.5 hrs, than 5.2 g methyl iodide in 15 ml DMF were added dropwise. After another 3 hrs the mixture was poured into ice water and the title product isolated by filtration in a yield of 7.5 g.

Workup

  1. additionwere added dropwise

Sources & evidence

ORD record
ord-0de7095bd6ab45469c4e0d001ceb86a0
Source dataset
uspto-grants-2006_08
Patent number
US07091345B2

Reaction notes

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