Acetic Acid → HCID 22033365, compound

HRID 1792304Notes

Reaction equation

HRID 1792304 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1.Br.C(O)(=O)C>O>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 22033200HCID 22033200, compound

Product 1

HCID 22033365HCID 22033365, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-[9-(3-dimethylaminopropylthio)nonyl]thiochroman (50 mg, 0.09 mmol), hydrobromic acid (0.13 ml, 48% aqueous solution) and acetic acid (0.15 ml) was heated for 8 hours. After the reaction was completed, water was added to the reaction solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and water, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure to give the title compound (60 ml, crude product) as a colorless oil. This compound thus obtained was used in the next reaction without further purification.

Workup

  1. temperaturewas heated for 8 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe residue was concentrated under reduced pressure

Sources & evidence

ORD record
ord-af50e64518f243c5af0707691d2b4dd0
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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