Isopropanol → Methyl nitro(1,3-thiazinan-2-ylidene)acetate

HRID 442301Notes

Reaction equation

HRID 442301 reaction equation
CS[C:3]1[S:4][CH2:5][CH2:6][CH2:7][N:8]=1.[N+:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])([O-:11])=[O:10].C(O)(C)C>[Cl-].[Zn+2].[Cl-].CCOCC>[N+:9]([C:12](=[C:3]1[NH:8][CH2:7][CH2:6][CH2:5][S:4]1)[C:13]([O:15][CH3:16])=[O:14])([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 17206Methyl 2-nitroacetateHCID 27820812-(methylsulfanyl)-5,6-dihydro-4H-1,3-thiazine

Product 1

HCID 71400745Methyl nitro(1,3-thiazinan-2-ylidene)acetate

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 221 g of 5,6-dihydro-2-(methylthio)-4H-1,3-thiazine (A. F. McKay et al., J. Am. Chem. Soc., 80, 3339 (1950) and 1 g of zinc chloride at about 100°, 202 g of methyl nitroacetate (S. Zen et al., Kogyo Kagaku Zasshi, 74, 70 (1971)) was added dropwise over a 30-minute period. The resulting mixture was heated for 4 hours at 95°-105°. 200 ml of isopropyl alcohol then was added to the hot mixture, then 400 ml of ether was added. The resulting mixture was filtered to give methyl nitro(tetrahydro-2H-1,3-thiazin-2-ylidene)-acetate (1A), as a pale yellow solid, m.p.: 107°-108° C.

Workup

  1. temperatureThe resulting mixture was heated for 4 hours at 95°-105°
  2. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-538a4fb5b6094e2996a88f051c9dd157
Source dataset
uspto-grants-1977_08
Patent number
US04045434

Reaction notes

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