5-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]thiadiazin-3-ylmethyl]-3-methylsulphanyl-1,3-dihydro-indol-2-one → HCID 66636326, compound

HRID 44285Notes

Reaction equation

HRID 44285 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][S:12][C:11](=[O:14])[N:10]([CH2:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20](=[O:25])[CH:19]4SC)[N:9]=2)=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][S:12][C:11](=[O:14])[N:10]([CH2:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20](=[O:25])[CH2:19]4)[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 666362955-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]thiadiazin-3-ylmethyl]-3-methylsulphanyl-1,3-dihydro-indol-2-one

Product 1

HCID 66636326HCID 66636326, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Powdered zinc (18.09 mmoles) is added to a solution of the compound obtained in Step D (27.68 mmoles) in glacial acetic acid (350 ml). The reaction mixture is stirred overnight at ambient temperature and then filtered. The filtrate is concentrated and then brought to pH 8-9 with saturated aqueous sodium bicarbonate solution and sonicated for 5 minutes. The solid formed is filtered off and then recrystallised from ethanol to yield the title product.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated
  3. customsonicated for 5 minutes
  4. customThe solid formed
  5. filtrationis filtered off
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-14a011fafd5a4972b2c7b80cf9b98555
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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