Methyl chloroformate → HCID 53952731, compound

HRID 1248004Notes

Reaction equation

HRID 1248004 reaction equation
[CH3:1][O:2][C:3](Cl)=[O:4].[N+:6]([CH:9]=[C:10]1[NH:15][CH2:14][CH2:13][CH2:12][S:11]1)([O-:8])=[O:7].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]([N:15]1[CH2:14][CH2:13][CH2:12][S:11][C:10]1=[CH:9][N+:6]([O-:8])=[O:7])=[O:4]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazine

Product 1

HCID 53952731HCID 53952731, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methoxycarbonyl chloride (5.7 g) in dichloromethane (60 ml) was added dropwise over a period of 30 minutes to a solution of 2-nitromethylene-tetrahydro-2H-1,3-thiazine (6.4 g) and triethylamine (10.4 ml) in dichloromethane (60 ml) at -20° C. under nitrogen. The reaction mixture was allowed to warm to ambient temperature over a period of 60 minutes and was then washed with 2% hydrochloric acid. The organic phase was dried (MgSO4) and the solvent was removed under reduced pressure. The residue was triturated with ethyl acetate to yield the required product as a crystalline solid m.p. 93°-95° C.

Workup

  1. washwas then washed with 2% hydrochloric acid
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-388883a9ef6f4b2db200b9e9dc9a7c0b
Source dataset
uspto-grants-1985_06
Patent number
US04521536

Reaction notes

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