Hydrochloric Acid → HCID 59486236, compound

HRID 409666Notes

Reaction equation

HRID 409666 reaction equation
Cl.C(OC(=O)[NH:8][C:9]1[C:14]([CH3:15])=[C:13]([O:16][CH3:17])[CH:12]=[C:11]([O:18][CH3:19])[C:10]=1[Cl:20])(C)(C)C>O1CCOCC1>[Cl:20][C:10]1[C:11]([O:18][CH3:19])=[CH:12][C:13]([O:16][CH3:17])=[C:14]([CH3:15])[C:9]=1[NH2:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86625458HCID 86625458, compound

Product 1

HCID 59486236HCID 59486236, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (91 mL, 360 mmol, 8 equiv, 4N in dioxane) is added dropwise to a cooled (10° C.) solution of (2-chloro-3,5-dimethoxy-6-methyl-phenyl)-carbamic acid tert-butyl ester (13.8 g, 45.7 mmol) in dioxane (150 mL), under an argon atmosphere. The reaction mixture is allowed to warm to RT, stirred for 24 h and concentrated. The residue is diluted with EtOAc, washed with a saturated aqueous solution of NaHCO3, and brine, dried (Na2SO4), filtered and concentrated. The residue is purified by crystallization from DCM/Hex to afford the title compound. ESI-MS: 202.0 [MH]+, TLC: Rf=0.37 (DCM).

Workup

  1. concentrationconcentrated
  2. additionThe residue is diluted with EtOAc
  3. washwashed with a saturated aqueous solution of NaHCO3, and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by crystallization from DCM/Hex

Sources & evidence

ORD record
ord-2cc2cefd34fd4cab9e955c4001061fb6
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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