2-(4-t-Butylphenoxy)thioacetamide → HCID 10134842, compound

HRID 1935593Notes

Reaction equation

HRID 1935593 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:11])[CH:8]=2)[C:3]1=[O:12].[C:13]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]([NH2:25])=[S:24])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>CC(C)=O>[C:13]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]2[S:24][CH:2]3[CH2:10][C:9]4[CH:8]=[C:7]([Cl:11])[CH:6]=[CH:5][C:4]=4[C:3]3([OH:12])[N:25]=2)=[CH:19][CH:18]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 27439122-(4-t-Butylphenoxy)thioacetamideHCID 113340692-Bromo-5-chloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 10134842HCID 10134842, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

At room temperature, 0.49 g of 2-bromo-5-chlorindan-1-on and 0.45 g of 2-(4-tert-butylphenoxy)-thioacetamide were dissolved in 10 ml of dry acetone, and the mixture was stirred at room temperature for 12 h. The precipitated hydrobromide was filtered off with suction and washed with acetone. The residue was suspended in a little ethyl acetate and treated with saturated sodium bicarbonate solution. The organic phase was separated off, dried over magnesium sulfate, filtered and concentrated under reduced pressure. This synthesis yielded 2-(4-tert-butylphenoxymethyl)-6-chloro-8,8a-dihydroindeno [1,2-d]thiazol-3a-ol having a melting point of 122-124° C.

Workup

  1. filtrationThe precipitated hydrobromide was filtered off with suction
  2. washwashed with acetone
  3. additiontreated with saturated sodium bicarbonate solution
  4. customThe organic phase was separated off
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89ecc1b48e754288b7f206b9123014bb
Source dataset
uspto-grants-2002_05
Patent number
US06387935B1

Reaction notes

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