Retinoyl chloride → Retinamide

HRID 429587

Reaction equation

HRID 429587 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18](Cl)=[O:19].O.[NH3:24]>O1CCCC1>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18]([NH2:24])=[O:19]

Participants

4

Reactant 2

HCID 10881705Retinoyl chlorideHCID 12896473Azane;hydrate

Product 1

HCID 5370221RetinamideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 g (0.031 mole) of retinoic acid chloride as prepared according to the procedure described in Example 2 was added to the mixture of 300 ml of ammonia water (35%) and 100 ml of tetrahydrofuran and then stirred at room temperature for 20 hours. The reaction solution was distilled under reduced pressure and then concentrated. The residue was extracted with methylene chloride. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, filtered and then distilled under reduced pressure to obtain 9.43 g (Yield 99%) of the desired retinamide.

Workup

  1. distillationThe reaction solution was distilled under reduced pressure
  2. concentrationconcentrated
  3. extractionThe residue was extracted with methylene chloride
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-6572553c177743bea7be0af2dd8a8236
Source dataset
uspto-grants-2001_11
Patent number
US06316644B1

Linked notes

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