Triethylamine → HCID 86737416, compound

HRID 1758040Notes

Reaction equation

HRID 1758040 reaction equation
Cl.[SH:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.Cl[CH2:14][C:15]([C:17](=[N:23][O:24][CH3:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=O>C(Cl)(Cl)Cl>[S:2]1[CH:14]=[C:15]([C:17](=[N:23][O:24][CH3:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 3017525Ethyl 4-chloro-2-(methoxyimino)-3-oxobutanoate

Product 1

HCID 86737416HCID 86737416, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2-mercaptoethylamine hydrochloride (10.0 g.) in chloroform (100 ml.) were added triethylamine (18.7 g.) and ethyl 2-chloroacetyl-2-methoxyiminoacetate (26.2 g., purity 70%) under ice-cooling and stirred at room temperature for 1.5 hours. After the resultant solution was concentrated in vacuo, water was added to the residue and extracted with diethyl ether four times. The extract was washed with a saturated aqueous solution of sodium chloride, and extracted with 10% hydrochloric acid 4 times. The hydrochloric acid extract was washed with diethyl ether twice and adjusted to pH 6.5 with a saturated aqueous solution of sodium bicarbonate, and further extracted with diethyl ether 4 times. The extract was dried over magnesium sulfate and concentrated in vacuo to give ethyl 2-(2,3-dihydro-4H-1,4-thiazin-5-yl)-2-methoxyiminoacetate (syn isomer, 5.2 g.), oil.

Workup

  1. temperaturecooling
  2. concentrationAfter the resultant solution was concentrated in vacuo, water
  3. additionwas added to the residue
  4. extractionextracted with diethyl ether four times
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. extractionextracted with 10% hydrochloric acid 4 times
  7. extractionThe hydrochloric acid extract
  8. washwas washed with diethyl ether twice
  9. extractionfurther extracted with diethyl ether 4 times
  10. dry with materialThe extract was dried over magnesium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-896fd9bd49834e4b8019045c94316ce2
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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