Hydrochloric Acid → HCID 136229043, compound

HRID 2296040Notes

Reaction equation

HRID 2296040 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].C(N(CC)CC)C.[C:13](=[N:18][OH:19])(Cl)[C:14]([CH3:16])=O.Cl>O1CCCC1>[N:18](=[C:13]1[C:14]([CH3:16])=[N:2][CH2:3][CH2:4][S:5]1)[OH:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 6399062N-Hydroxy-2-oxopropanimidoyl chloride

Product 1

HCID 136229043HCID 136229043, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.27 g (0.02 mol) of cysteamine hydrochloride are suspended in 40 ml of absolute tetrahydrofuran and treated with 5.55 ml (0.04 mol) of triethylamine to free the base. The mixture is stirred for 15 minutes at room temperature and then cooled down to about -30° C. At this temperature a solution of 2.42 g (0.02 mol) of pyruvyl chloride 1-oxime in 10 ml of absolute tetrahydrofuran is added dropwise. The reaction mixture is allowed to warm to room temperature while being well stirred. After two hours ice-water and then dilute hydrochloric acid are added until a pH of 5-6 has been attained. The reaction mixture is extracted twice with ethyl acetate and the organic phase is washed with sodium chloride solution, dried over anhydrous sodium sulfate and finally evaporated. The resulting crystalline residue is treated with active charcoal. After recrystallization from hot ethyl acetate and n-hexane there is obtained pure 2-oxo-5,6-dihydro-3-methyl-2H-1,4-thiazine oxime, m.p. 197° C. (with decomposition).

Workup

  1. temperaturecooled down to about -30° C
  2. temperatureto warm to room temperature
  3. stirringwhile being well stirred
  4. extractionThe reaction mixture is extracted twice with ethyl acetate
  5. washthe organic phase is washed with sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customfinally evaporated
  8. additionThe resulting crystalline residue is treated with active charcoal
  9. customAfter recrystallization from hot ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-b4be30f92ed94f20b089b4faa3f8e9ce
Source dataset
uspto-grants-1984_01
Patent number
US04427687

Reaction notes

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