Water → HCID 15450533, compound

HRID 2299571Notes

Reaction equation

HRID 2299571 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][CH:7]=[C:8]([C:9]([OH:11])=[O:10])[C:4]=2[CH:3]=1.SC1C=C[C:18]([OH:21])=[CH:17]C=1.N1C=CC=CC=1.O>C(OC(=O)C)(=O)C>[C:18]([O:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][CH:7]=[C:8]([C:9]([OH:11])=[O:10])[C:4]=2[CH:3]=1)(=[O:21])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 2401474-MercaptophenolHCID 114128975-Hydroxybenzo[b]thiophene-3-carboxylic acid

Product 1

HCID 15450533HCID 15450533, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

5-Hydroxybenzo[b]thiophene-3-carboxylic acid (11) (1,140 mg) prepared in above (1) was dissolved in acetic anhydride (2 ml), pyridine (4 ml). After 3 hours, water was added and the mixture was continuously stirred under ice-cooling for 1.5 hours. The deposited crystals were filtered, washed with water and dried to provide 1,349 mg of the title compound (12). Yield: 97.3% mp 239-240° C. 1H NMR δ (CDCl3), 300 MHz; 2.37(H, s), 7.20 (1H, dd, J=2.4 and 8.7 Hz), 7.87 (1H, d, J=8.7 Hz), 8.34 (1H, d, J=2.4 Hz), 8.57 (1H, s);

Workup

  1. temperaturecooling for 1.5 hours
  2. filtrationThe deposited crystals were filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-08bbc2bc40744babb4631d0ce3247d26
Source dataset
uspto-grants-2002_12
Patent number
US06495702B2

Reaction notes

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