Hydrochloric Acid → HCID 9953017, compound

HRID 1900041Notes

Reaction equation

HRID 1900041 reaction equation
[CH3:1][C:2]([CH3:16])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3](Cl)=[O:4].[NH2:17][C:18]1[C:19]([O:29][CH3:30])=[CH:20][CH:21]=[C:22]2[C:27]=1[O:26][CH2:25][CH2:24][C:23]2=[O:28].C(N(CC)CC)C.Cl>ClCCl>[CH3:30][O:29][C:19]1[C:18]([NH:17][C:3](=[O:4])[C:2]([CH3:16])([CH3:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:27]2[C:22]([C:23](=[O:28])[CH2:24][CH2:25][O:26]2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10035494HCID 10035494, compoundHCID 156564322,2-Dimethyldodecanoyl chloride

Product 1

HCID 9953017HCID 9953017, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

127 mg of 2,2-dimethyldodecanoyl chloride was added to a solution of 98 mg of 8-amino-7-methoxy-4-chromanone and 0.07 ml of triethylamine in 2 ml of dichloromethane, and the mixture was stirred at room temperature for 12 hr. 15 ml of 2N hydrochloric acid was added thereto, and the mixture was extracted with ethyl acetate (25 ml×2). The extract was washed with 25 ml of brine, dried over anhydrous magnesium sulfate, filtered, concentrated and purified by silica gel column chromatography (hexane/ethyl acetate=3:2) to give 198 mg of the intended title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (25 ml×2)
  2. washThe extract was washed with 25 ml of brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (hexane/ethyl acetate=3:2)

Sources & evidence

ORD record
ord-3bede566fa2444d996ba4f82eb26f184
Source dataset
uspto-grants-1996_11
Patent number
US05574061

Reaction notes

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