Hydrochloric Acid → HCID 54675792, compound

HRID 1764451Notes

Reaction equation

HRID 1764451 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[OH:12][C:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]=2[O:16][S:15](=O)(=O)[CH:14]=1.Cl>CN(C=O)C>[OH:12][C:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:17]=2[O:16][S:15][C:14]=1[C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 24758Sodium hydrideHCID 22768440HCID 22768440, compound

Product 1

HCID 54675792HCID 54675792, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenylisocyanate (20.5 mmol) was added to a cooled DMF solution (25 ml) containing 20.5 mmol of NaH and 5.0 g (18.3 mmol) of 4-hydroxy-8-phenyl-1,2-benzoxathiin-2,2-dioxide. The resultant mixture was heated at 75° for 2.5 hours. The mixture was cooled, poured into ice-H2O (100 ml) and acidified with HCl. The resultant precipitate was collected by filtration and gave 6.70 g (93.3%) of the expected product, mp. 175°. The crude product was purified by recrystallization from 2-PrOH/hexane to give the analytical sample, mp. 181°-183°.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-c87ce72f17004634878156d60521408f
Source dataset
uspto-grants-1978_09
Patent number
US04116961

Reaction notes

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