1-Methylimidazole → 2-nitro-1-(4-nitrophenyl)-2-(tetrahydro-2H-1,3-thiazine-2-ylidene)ethanone

HRID 597748Notes

Reaction equation

HRID 597748 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].CN1C=CN=C1.[N+:19]([CH:22]=[C:23]1[NH:28][CH2:27][CH2:26][CH2:25][S:24]1)([O-:21])=[O:20]>C(COC)OC.C(Cl)Cl>[N+:19]([C:22](=[C:23]1[NH:28][CH2:27][CH2:26][CH2:25][S:24]1)[C:8]([C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:9])([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 13901-MethylimidazoleHCID 85024-Nitrobenzoyl chlorideHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazine

Product 1

HCID 731795252-nitro-1-(4-nitrophenyl)-2-(tetrahydro-2H-1,3-thiazine-2-ylidene)ethanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution/suspension of 20.4 g of p-nitrobenzoyl chloride in 25 ml of monoglyme was added dropwise at 5°-10° to a solution of 9.09 g of N-methylimidazole in 75 ml of monoglyme and the mixture was stirred for an additional 30 minutes at 5°-10°, after which was added dropwise (same temperature) a solution/suspension of 16.0 g of tetrahydro-2-(nitromethylene)-2H-1,3-thiazine in 25 ml of monoglyme, after which the stirred mixture was allowed to warm to room temperature and stirred for 96 hours. The mixture then was taken up in methylene chloride, washed with water and saturated sodium chloride solution, dried (Na2SO4) and the solvent evaporated under reduced pressure to give an oil which was chromatographed on florosil using methylene chloride as eluent to give a gum, which was washed with ether to give 17, as a yellow solid, m.p.: 158°-160.5°.

Workup

  1. additionafter which was added dropwise (same temperature)
  2. stirringstirred for 96 hours
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated under reduced pressure
  6. customto give an oil which
  7. customwas chromatographed on florosil
  8. customto give a gum, which
  9. washwas washed with ether

Sources & evidence

ORD record
ord-3530d07c0ccf487db3138ce01099d390
Source dataset
uspto-grants-1977_03
Patent number
US04015001

Reaction notes

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