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Hydrochloric Acid → HCID 68408133, compound

HRID 505335
Notes
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Reaction equation

HRID 505335 reaction equation
[NH2:1][C:2]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([Cl:15])[C:3]=1[C:4](N(OC)C)=[O:5].[CH2:16](OCC)C.Cl>C1COCC1.O>[NH2:1][C:2]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([Cl:15])[C:3]=1[C:4](=[O:5])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86608958HCID 86608958, compound

Product 1

HCID 68408133HCID 68408133, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028Tetrahydrofuran
Solvent

Procedure

2-Amino-3,6-dichloro-N-methoxy-N-methyl-benzamide (2491 mg, 10 mmol) were dissolved in THF (100 ml). At −78° C. under nitrogen 1.6 M methyllithium solution in diethylether (25.0 ml, 40 mmol) were added dropwise and the reaction was allowed to reach room temperature and was stirred over night. The reaction was cooled in an icebath and 2N aqueous hydrogen chloride solution (30 ml) were added and the reaction was stirred for 30 min (r.t.). The reaction was diluted with water and extracted twice with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (CH2Cl2) to yield the product as an orange oil (565 mg, 28%).

Workup

  1. customto reach room temperature
  2. additionwere added
  3. stirringthe reaction was stirred for 30 min (r.t.)
  4. extractionextracted twice with diethyl ether
  5. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-ef072b3d6e5d4885b5a1e158d746ad74
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07781441B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes