Ammonia → HCID 18442916, compound

HRID 458712Notes

Reaction equation

HRID 458712 reaction equation
[CH3:1][O:2][C:3]([CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[CH:28][C:27]3[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=3[CH:21]=2)=[CH:12][CH:11]=1)[C:6](O)=[O:7])=[O:4].S(Cl)(Cl)=O.[NH3:38]>C1C=CC=CC=1.C(OCC)(=O)C>[C:6]([CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[CH:28][C:27]3[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=3[CH:21]=2)=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])(=[O:7])[NH2:38]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 18442904HCID 18442904, compound

Product 1

HCID 18442916HCID 18442916, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(methoxycarbonyl)-3-[4-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoxy)ethoxy]phenyl]propionic acid (2.40 g, 5.29 mmol) in benzene (20 ml) at room temperature is added thionyl chloride (0.76 g, 6.34 mmol). Then the mixture is heated at 80° C. for 90 min. After cooled to room temperature, the solvent is removed under a vacuum. To the residue is added 28% ammonia solution (5.49 ml, 79.30 mmol) at room temperature. The mixture is stirred for 30 min, dissolved in ethyl acetate (20 ml), washed with brine (3×15 ml), dried over sodium sulfate, and concentrated. The crude product is crystallized from ethanol to give title compound (1.35 g, 56%). HRMS calcd for C27H35NO5: 453.5786. Found: 453.5784. MA calcd for C27H35NO5: C, 71.50%; H, 7.78%; N, 3.09. Found: C, 71.52%; H, 7.76%; N, 3.12%.

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe solvent is removed under a vacuum
  3. washwashed with brine (3×15 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product is crystallized from ethanol

Sources & evidence

ORD record
ord-0ad53d5dec164e34a545135ff6b1b333
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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