Methanol → HCID 85945283, compound

HRID 1834882Notes

Reaction equation

HRID 1834882 reaction equation
[OH-].[Na+].CO.C1(C)C=CC=CC=1.C([S:15][CH2:16][C:17]([N:19]([CH3:26])[CH:20]([CH3:25])[CH2:21][N+:22]([O-])=[O:23])=[O:18])(=O)C>O>[N:22](=[C:21]1[CH:20]([CH3:25])[N:19]([CH3:26])[C:17](=[O:18])[CH2:16][S:15]1)[OH:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 14798Sodium HydroxideHCID 54324505HCID 54324505, compound

Product 1

HCID 85945283HCID 85945283, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.6 g of sodium hydroxide, 100 ml of methanol and 100 ml of toluene was charged into a flask and stirred vigorously while adding 23 g of 2-(acetylthio)-N-methyl-N-(1-nitro-2-propyl)acetamide, over a 5 minute period at 30°-40° C. The reaction mixture was stirred at 40° C for 8 hours, then stirred overnight at room temperature. The mixture was stripped of solvents under reduced pressure. The solid residue was dissolved in 200 ml of water. The mixture was filtered and the filtrate was acidified with hydrochloric acid. The solid which precipitated was filtered, washed with water and dried at room temperature. The solid product was recrystallized from isopropanol to yield 5.0 g of 2-oximino-3,4-dimethyltetrahydro-1,4-thiazin-5-one, m.p. 205° C.

Workup

  1. stirringThe reaction mixture was stirred at 40° C for 8 hours
  2. stirringstirred overnight at room temperature
  3. filtrationThe mixture was filtered
  4. customThe solid which precipitated
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried at room temperature
  8. customThe solid product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-2c694138e4a046fb8a4376e0bde2d6e5
Source dataset
uspto-grants-1978_01
Patent number
US04071627

Reaction notes

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