Sulfuric Acid → HCID 54000495, compound

HRID 1719569Notes

Reaction equation

HRID 1719569 reaction equation
[CH3:1][NH:2][C:3]([O:5][N:6]=[C:7]([S:9][CH3:10])[CH3:8])=[O:4].[CH3:11][O:12][CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[S:16]Cl.C(N(CC)CC)C.S(=O)(=O)(O)O>ClC(Cl)C>[CH3:1][N:2]([S:16][N:15]([CH2:14][CH2:13][O:12][CH3:11])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:3]([O:5][N:6]=[C:7]([S:9][CH3:10])[CH3:8])=[O:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 4109MethomylHCID 8471TriethylamineHCID 54297536HCID 54297536, compound

Product 1

HCID 54000495HCID 54000495, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A 14.6 g (0.09 mole) quantity of S-methyl N-[(methylcarbamoyl)oxy]thioacetimidate was poured into 100 ml of a dichloroethane solution containing 22.75 g (0.1 mole) of N-methoxyethyl-N-methoxycarbonylethylaminosulfenyl-chloride. The mixture was agitated by a stirred and 18 g (0.18 mole) of triethylamine was added dropwise at less than 5° C. over a period of 30 minutes. Thereafter the mixture was agitated at the same temperature for 1 hour. A 5% aqueous solution of sulfuric acid was added to the mixture until a pH of 6 was achieved. The dichloroethane solution was washed with a 5% aqueous solution of sodium hydrogencarbonate and with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated at reduced pressure, giving 31 g of a yellow brown oily product in a yield of 87.8%.

Workup

  1. stirringa stirred
  2. stirringThereafter the mixture was agitated at the same temperature for 1 hour
  3. washThe dichloroethane solution was washed with a 5% aqueous solution of sodium hydrogencarbonate and with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-11b4670856a645219508d1d0c2dd6795
Source dataset
uspto-grants-1985_09
Patent number
US04540708

Reaction notes

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