Hydrochloric Acid → HCID 58303835, compound

HRID 1886981Notes

Reaction equation

HRID 1886981 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.O.O.O.O.O.O.O.[S-2:28].[Na+].[Na+].CCOCC.Cl>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[SH:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 73972Sodium sulfide nonahydrateHCID 143561211-(Benzyloxy)-2-chloro-3-nitrobenzene

Product 1

HCID 58303835HCID 58303835, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 8.56 g (32.5 mmol) of 1-(benzyloxy)-2-chloro-3-nitrobenzene in 120 mL of DMF was added 15.6 g (64.9 mmol) of pulverized sodium sulfide nonahydrate. The mixture was stirred vigorously at 22° C. for 30 hours and then poured into a vigorously stirred mixture of ether and 1 N HCl. The organic layer was washed with water then brine, dried (Na2SO4), and evaporated. The residue was crystallized from dichloromethane (DCM) and hexane to give 2-(benzyloxy)-6-nitrobenzenethiol.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialbrine, dried (Na2SO4)
  3. customevaporated
  4. customThe residue was crystallized from dichloromethane (DCM) and hexane

Sources & evidence

ORD record
ord-1a9ba1d883fc4afa9f25825215dda737
Source dataset
uspto-grants-2013_08
Patent number
US08501727B2

Reaction notes

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