Hydrochloric Acid → HCID 19601772, compound

HRID 658000Notes

Reaction equation

HRID 658000 reaction equation
[C:1]([C:5]1[CH:6]=[C:7](C(N(OC)C)=O)[CH:8]=[C:9]([CH:16]=1)[C:10](N(OC)C)=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH3:23][Mg]Br.Cl.CC[O:29][CH2:30][CH3:31]>C1COCC1>[C:10]([C:9]1[CH:16]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=[C:7]([C:30](=[O:29])[CH3:31])[CH:8]=1)(=[O:11])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 58045996HCID 58045996, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19601772HCID 19601772, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 41 three-neck flask with a mechanical stirrer, a solution of 5-tert-butyl-N,N′-dimethoxy-N,N′-dimethylisophthalamide (O5.106; 254 g, 560 mmol) in THF (700 ml) was slowly added dropwise within 2 h to methylmagnesium bromide (3 M in Et2O, 1.49 1, 4.48 mol). The solution was cooled during the addition, such that the temperature was kept between −10° C. and +5° C. On completion of addition, the cooling was removed and the reaction solution was stirred at RT for 16 h. The reaction solution was then added slowly to a cooled mixture of HCl (1 M, 500 ml) and ice. During this hydrolysis, the pH was kept between 3 and 6 by the addition of concentrated HCl. On completion of addition, MtB ether (1 l ) was added. The phases were separated and the aqueous phase was extracted with MtB ether (1×500 ml). The combined organic phases were dried (MgSO4), and the solvent was removed under reduced pressure. The product was obtained as a colorless oil (123 g). LC-MS rt: 1.50 min [M+H]+: 219 (met. a)

Workup

  1. temperatureThe solution was cooled during the addition, such that the temperature
  2. customwas kept between −10° C. and +5° C
  3. additionOn completion of addition
  4. customthe cooling was removed
  5. additionThe reaction solution was then added slowly to a cooled mixture of HCl (1 M, 500 ml) and ice
  6. customDuring this hydrolysis
  7. additionwas added
  8. customThe phases were separated
  9. extractionthe aqueous phase was extracted with MtB ether (1×500 ml)
  10. dry with materialThe combined organic phases were dried (MgSO4)
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4bf42bfe679041c39e35e173fb06d0bc
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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