Sulfuric Acid → HCID 15590585, compound

HRID 1719568Notes

Reaction equation

HRID 1719568 reaction equation
[CH3:1][NH:2][C:3](=[O:16])[O:4][C:5]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH3:17][O:18][CH2:19][CH2:20][N:21]([CH2:24][CH2:25][C:26]#[N:27])[S:22]Cl.C(N(CC)CC)C.S(=O)(=O)(O)O>ClCCl>[CH3:17][O:18][CH2:19][CH2:20][N:21]([CH2:24][CH2:25][C:26]#[N:27])[S:22][N:2]([CH3:1])[C:3](=[O:16])[O:4][C:5]1[C:13]2[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 2566CarbofuranHCID 8471TriethylamineHCID 53771065HCID 53771065, compound

Product 1

HCID 15590585HCID 15590585, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 19.9 g (0.09 mole) quantity of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methyl-carbamate was poured into 100 ml of a dichloromethane solution containing 19.45 g (0.1 mole) of N-(2-methoxyethyl)-N-cyanoethylaminosulfenyl-chloride. The mixture was agitated by a stirrer and 18 g (0.18 mole) of triethylamine was added dropwise thereto at less than 10° C. over a period of 30 minutes. Thereafter the mixture was stirred at the same temperature for 2 hours. A 5% aqueous solution of sulfuric acid was added to the mixture until a pH of 6 was achieved. The dichloromethane 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 31.8 g of a yellowish brown oily product in a yield of 84.0%.

Workup

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

Sources & evidence

ORD record
ord-655b15c22ca749288f59bd5d8572b99f
Source dataset
uspto-grants-1985_09
Patent number
US04540708

Reaction notes

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