Methyl chloroformate → Methyl 5,6-dihydro-2-(2-methoxy-1-nitro-2-oxoethylidene)-2H-1,3-thiazine-3(4H)-carboxylate

HRID 616880Notes

Reaction equation

HRID 616880 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Na].[N+:7]([C:10](=[C:15]1[NH:20][CH2:19][CH2:18][CH2:17][S:16]1)[C:11]([O:13][CH3:14])=[O:12])([O-:9])=[O:8]>C1COCC1>[CH3:14][O:13][C:11](=[O:12])[C:10](=[C:15]1[N:20]([C:2]([O:4][CH3:5])=[O:3])[CH2:19][CH2:18][CH2:17][S:16]1)[N+:7]([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 5360545SodiumHCID 71400745Methyl nitro(1,3-thiazinan-2-ylidene)acetate

Product 1

HCID 73676598Methyl 5,6-dihydro-2-(2-methoxy-1-nitro-2-oxoethylidene)-2H-1,3-thiazine-3(4H)-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° a solution of 16.0 g of methyl chloroformate in THF was added dropwise to a solution of the sodium derivative of 32.7 g of methyl nitro(tetrahydro-2H-1,3-thiazin-2-ylidene)acetate (3A; Example 2, Ser. No. 554,371) in THF. The stirred solution was then allowed to warm to room temperature and stirred overnight. The solvent was evaporated under reduced pressure and the residue was poured into ether. The ether phase was washed with water, dried (MgSO4) and the solvent evaporated under reduced pressure. The resulting oil was mixed with pentane to give 3, as yellow crystals, m.p.: 71°-2°.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was poured into ether
  3. washThe ether phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated under reduced pressure
  6. additionThe resulting oil was mixed with pentane
  7. customto give 3

Sources & evidence

ORD record
ord-b3a014cffe4a4e05aa640fdd8cedd2a0
Source dataset
uspto-grants-1978_02
Patent number
US04076813

Reaction notes

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