1-Methylimidazole → phenyl nitro(tetrahydro-2H-1,3-thiazin-2-ylidene)acetate

HRID 1657723Notes

Reaction equation

HRID 1657723 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].CN1C=CN=C1.[N+:17]([CH:20]=[C:21]1[NH:26][CH2:25][CH2:24][CH2:23][S:22]1)([O-:19])=[O:18]>O1CCCC1>[N+:17]([C:20](=[C:21]1[NH:26][CH2:25][CH2:24][CH2:23][S:22]1)[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3])([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 15891Phenyl chloroformateHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazine

Product 1

HCID 85867565phenyl nitro(tetrahydro-2H-1,3-thiazin-2-ylidene)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution 17.2 g of phenyl chloroformate in 25 ml of tetrahydrofuran was added dropwise to a solution of 9.09 g of 1-methylimidazole in 75 ml of tetrahydrofuran, the temperature of the reaction mixture being kept below 10° by means of an ice bath. Thirty minutes after the addition was completed, a solution of 16.0 g of (B) in 150 ml of tetrahydrofuran was added rapidly dropwise. The stirred mixture then was allowed to warm to room temperature and stirred for two days. The mixture was extracted with methylene chloride, the extracts washed with water, dried (MgSO4) and the solvent stripped off to give an oil. The oil was triturated first with a mixture of methanol and water, then with a cold mixture of methanol and ether to give as residue an orange-yellow solid, which on recrystallization from ethanol gave (66), as a pale yellow solid, m.p.: 95°-6°.

Workup

  1. customthe temperature of the reaction mixture being kept below 10° by means of an ice bath
  2. additionThirty minutes after the addition
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe extracts washed with water
  5. dry with materialdried (MgSO4)
  6. customto give an oil
  7. customThe oil was triturated first with a mixture of methanol and water
  8. additionwith a cold mixture of methanol and ether
  9. customto give as residue an orange-yellow solid, which
  10. customon recrystallization from ethanol

Sources & evidence

ORD record
ord-d0f35f12391142968468b828982198a0
Source dataset
uspto-grants-1976_06
Patent number
US03962234

Reaction notes

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