Sodium Hydroxide → 2-nitromethylenetetrahydro-2H-1,3-thiazine

HRID 1732090Notes

Reaction equation

HRID 1732090 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][SH:5].[OH-].[Na+].Cl[C:9](Cl)(Cl)[CH2:10][N+:11]([O-:13])=[O:12]>CO>[N+:11]([CH:10]=[C:9]1[NH:1][CH2:2][CH2:3][CH2:4][S:5]1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 974361-Propanethiol, 3-amino-HCID 109541031,1,1-Trichloro-2-nitroethane

Product 1

HCID 428532-nitromethylenetetrahydro-2H-1,3-thiazineYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
0 °C

Procedure

Into 50 ml of methanol was added 8.1 g of 1-amino-3-propanethiol, followed by stirring, to be completely dissolved therein. Then, the mixture was cooled to 0° C. While stirring the solution, about 1/3-aliquot of a solution of 5.0 g of caustic soda dissolved in 40 ml of methanol was added dropwise thereinto, and the remainder of about 2/3-aliquot of the solution and a solution of 5.4 g of 2,2,2-trichloro-1-nitroethane diluted in 20 ml of methanol were added dropwise slowly over 50 minutes, and the reaction was carried out for one hour. During the dropwise addition, the liquid temperature was maintained at lower than 10° C. (about 8° C.). After the reaction carried out for one hour, the procedure of the post-treatments as described in Example 1 was followed to obtain 4.20 g of tetrahydro-2-(nitromethylene)-1,3thiazine (yield: 86.8%).

Workup

  1. dissolutionto be completely dissolved
  2. stirringWhile stirring the solution
  3. additionwas added dropwise
  4. additionwere added dropwise slowly over 50 minutes
  5. additionDuring the dropwise addition
  6. temperaturethe liquid temperature was maintained at lower than 10° C. (about 8° C.)
  7. waitAfter the reaction carried out for one hour

Sources & evidence

ORD record
ord-ebe362574f2d45e0a8ccd267266d9602
Source dataset
uspto-grants-1986_11
Patent number
US04625025

Reaction notes

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