Methanethiol → HCID 14722454, compound

HRID 1031669Notes

Reaction equation

HRID 1031669 reaction equation
Br[CH:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:5]=2[O:4][CH2:3]1.[CH3:25][SH:26].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:17][S:14]([NH:13][C:11]1[C:10]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:9][C:6]2[C:7](=[O:8])[CH:2]([S:26][CH3:25])[CH2:3][O:4][C:5]=2[CH:12]=1)(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 8471TriethylamineHCID 10621601HCID 10621601, compound

Product 1

HCID 14722454HCID 14722454, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of methylene chloride were dissolved 2.06 g of 3-bromo-2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one and 480 mg- of methylmercaptan. Thereto was added 2.02 g of triethylamine at 0°-5° C. The mixture was stirred for 1 hour at room temperature. The reaction mixture was introduced into 30 ml of water. The organic layer was separated, washed with water, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 50 : 1 mixture of toluene and ethyl acetate) to obtain 900 mg (yield: 47.4%) of 2,3-dihydro-7-methylsulfonylamino-3-methylthio-6-phenoxy-4H-1-benzopyran-4-one.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by a column chromatography (eluant
  6. additiona 50 : 1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-9d784d8d52ff429ba9cede2d3ed95035
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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