Ethanethiol → HCID 20329871, compound

HRID 2058097Notes

Reaction equation

HRID 2058097 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([NH:6][CH2:7][C:8]2[CH:22]=[CH:21][C:11]([O:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16]CC)=[O:15])=[C:10](OC)[CH:9]=2)=[CH:4][CH:3]=1.C(S)C.[H-].[Na+]>CN(C)C=O>[CH3:20][C:13]1([CH3:19])[C:14](=[O:16])[O:15][C:21]2[CH:22]=[C:8]([CH2:7][NH:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:26][CH:25]=3)[CH:9]=[CH:10][C:11]=2[O:12]1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 20329833HCID 20329833, compound

Product 1

HCID 20329871HCID 20329871, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 500 mg of ethyl 2-[4-(4-chloroanilinomethyl)-2-methoxyphenoxy]-2-methylpropionate, 206 mg of ethanethiol, 159 mg of 50% sodium hydride and 10 ml of dimethylformamide is heated at 100° C. for 3 hours. The reaction mixture is poured into ice-water and washed with ether. The aqueous layer is adjusted to pH 2 with 10% hydrochloric acid and extracted with ether. The extract is washed with water, dried and concentrated. The residue is pulverized with a mixture of diisopropyl ether and n-hexane and the crystals are collected by filtration to give 250 mg of 3,3-dimethyl-7-(4-chloroanilinomethyl)-1,4-benzodioxan-2-one, mp 97° to 98° C. From the mother liquor 60 mg of the same compound is further obtained.

Workup

  1. washwashed with ether
  2. extractionextracted with ether
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated
  6. additionThe residue is pulverized with a mixture of diisopropyl ether and n-hexane
  7. filtrationthe crystals are collected by filtration

Sources & evidence

ORD record
ord-f49b504b87e948d89bbe89fa9184544b
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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