Ammonia → HCID 178510717, compound

HRID 1577546

Reaction equation

HRID 1577546 reaction equation
[C:1]([C:9]1[S:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[C:10]=1[OH:18])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:19]>O>[NH2:19]/[C:1](/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[C:9]1\[C:10](=[O:18])[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[S:13]\1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 4712192Methanone, (3-hydroxybenzo[b]thien-2-yl)phenyl-

Product 1

HCID 178510717HCID 178510717, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 10.0 gm (0.0393 mol) of 2-benzoylbenzo[b]-thiophen-3-ol, 60 cc of concentrated aqueous ammonia and 250 cc of ethanol was heated for 20 hours at a temperature of 120° C. after introducing 5 bar of ammonia gas into the vessel. After cooling, the mixture was stirred into 1.5 liters of water, the precipitated pale yellow reaction product was filtered off with suction, washed thoroughly several times with 50 cc each of water and dried in the air. 4.23 gm (42% of theory) of yellow crystals, m.p. 121°-122° C., were obtained (after twice recrystallizing from petroleum ether/ethyl acetate 1:1 using activated carbon) and were found to be completely identical with the product obtained in Example 1 based on elemental analysis, IR and UV spectra.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated pale yellow reaction product was filtered off with suction
  3. washwashed thoroughly several times with 50 cc each of water
  4. customdried in the air
  5. custom4.23 gm (42% of theory) of yellow crystals, m.p. 121°-122° C., were obtained (
  6. customafter twice recrystallizing from petroleum ether/ethyl acetate 1:1 using activated carbon) and

Sources & evidence

ORD record
ord-5d388c9bf3fc411c8812ac7ceb401c01
Source dataset
uspto-grants-1981_09
Patent number
US04288437

Linked notes

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