1-Methylimidazole → HCID 131710733, compound

HRID 2397542Notes

Reaction equation

HRID 2397542 reaction equation
Cl[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](OCC)=O.CN1C=CN=C1.[N+](C=C1[NH:27][CH2:26][CH2:25][CH2:24][S:23]1)([O-])=O.CC[O:30]CC>O1CCCC1.O.C(Cl)Cl>[S:23]1[CH2:24][CH2:25][CH2:26][NH:27][C:2]1=[CH:6][C:5](=[O:30])[S:4][CH2:3][CH3:7]

Participants

8

Reactant 4

HCID 13901-MethylimidazoleHCID 3283Diethyl EtherHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazineHCID 12993676Ethyl 3-chlorothiophene-2-carboxylate

Product 1

HCID 131710733HCID 131710733, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 13.7 g of ethyl chlorothiolformate in 50 ml of dry tetrahydrofuran was added to 9.0 g of 1-methylimidazole in 200 ml of dry tetrahydrofuran at 5°, over a 20-minute period. The mixture was stirred at 5° for 30 minutes, then 16.0 g of 31B was added all at once, and the stirred mixture was allowed to slowly warm to room temperature and was stirred overnight. The solvent was stripped, the residue dissolved in a mixture of water and methylene chloride. The two phases were separated, the water phase was extracted with methylene chloride, the methylene chloride solutions were combined, dried (MgSO4), filtered and the solvent evaporated under reduced pressure, to leave an oil. The oil was stirred with a mixture of water and ether; solid material was filtered off and recrystallized from ethyl alcohol to give nitro(tetrahydro-2H-1,3-thiazin-2-ylidene ethanethioic acid, S-ethyl ester (31C) as a pale yellow solid, m.p.: 124°-124.5°.

Workup

  1. stirringwas stirred overnight
  2. customThe two phases were separated
  3. extractionthe water phase was extracted with methylene chloride
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customto leave an oil
  8. filtrationsolid material was filtered off
  9. customrecrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-1ef8cce16b9347ba9ea1c1d5682b0390
Source dataset
uspto-grants-1977_05
Patent number
US04022775

Reaction notes

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