2-nitromethylenetetrahydro-2H-1,3-thiazine → 2-(5,6-Dihydro-4H-1,3-thiazin-2-yl)-N,N-dimethyl-2-nitroethen-1-amine

HRID 1576496Notes

Reaction equation

HRID 1576496 reaction equation
[N+:1]([CH:4]=[C:5]1[NH:10][CH2:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>C(Cl)(Cl)Cl>[S:6]1[CH2:7][CH2:8][CH2:9][N:10]=[C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:13][N:14]([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 428532-nitromethylenetetrahydro-2H-1,3-thiazineHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 538694182-(5,6-Dihydro-4H-1,3-thiazin-2-yl)-N,N-dimethyl-2-nitroethen-1-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

8.0 G OF TETRAHYDRO-2-(NITROMETHYLENE)-2H-1,3-thiazine, prepared as described in Example 2 of Ser. No. 554,361, 5.95 g of N,N-dimethylformamide dimethyl acetal and 25 ml of chloroform were mixed and the mixture was refluxed for about 16 hours. The solvent then was evaporated under reduced pressure to leave a dark orange solid. Recrystallization from ethyl acetate and methanol gave (1), as a light orange solid, m.p.: 168.5°-170°.

Workup

  1. temperaturethe mixture was refluxed for about 16 hours
  2. customThe solvent then was evaporated under reduced pressure
  3. customto leave a dark orange solid
  4. customRecrystallization from ethyl acetate and methanol

Sources & evidence

ORD record
ord-8bb9d52282b845a8a9bd24360ae11130
Source dataset
uspto-grants-1976_09
Patent number
US03981871

Reaction notes

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