Triethylamine → HCID 67707262, compound

HRID 1450326Notes

Reaction equation

HRID 1450326 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][CH:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:7][S:6]1(=[O:21])=[O:20])=[N+]=[N-].C(N(CC)CC)C>C(Cl)Cl>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][S:10][CH:8]2[CH2:7][S:6](=[O:21])(=[O:20])[CH:5]([CH2:4][NH2:1])[CH2:9]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 18924036HCID 18924036, compound

Product 1

HCID 67707262HCID 67707262, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution, under argon, of 1.4 g of product from Example 179 in 14 ml of dry methylene chloride is treated with 1.19 ml of triethylamine. Hydrogen sulfide gas is slowly bubbled through the cold solution for 20 minutes (the excess gas is trapped in a flask containing an aqueous solution of 5.25% sodium hypochlorite). The mixture is stirred at 0° C. for 2 hours, the flask flushed for 20 minutes with argon and the reaction is concentrated in vacuo. The residue is purified by chromatography (silica gel: 10-100% ethyl acetate/hexane, 5% methyl alcohol/ethyl acetate) to give 0.757 g of the desired product (mixture of isomers).

Workup

  1. customHydrogen sulfide gas is slowly bubbled through the cold solution for 20 minutes (the excess gas
  2. customis trapped in a flask
  3. additioncontaining an aqueous solution of 5.25% sodium hypochlorite)
  4. customthe flask flushed for 20 minutes with argon
  5. concentrationthe reaction is concentrated in vacuo
  6. customThe residue is purified by chromatography (silica gel: 10-100% ethyl acetate/hexane, 5% methyl alcohol/ethyl acetate)

Sources & evidence

ORD record
ord-470453cdf6434725b1c1d0c60641f572
Source dataset
uspto-grants-1997_02
Patent number
US05602118

Reaction notes

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