Water → HCID 20492177, compound

HRID 434779Notes

Reaction equation

HRID 434779 reaction equation
P(Cl)(Cl)(Cl)=O.[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][S:12][CH2:13][CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25].O.[CH:27]([OH:30])(C)C>CN(C)C=O>[CH:27]([C:10]1[O:6][C:7]([CH2:11][S:12][CH2:13][CH2:14][N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])=[CH:8][CH:9]=1)=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 24813Phosphorus oxychlorideHCID 132542762-(2-{[(Furan-2-yl)methyl]sulfanyl}ethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 20492177HCID 20492177, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of phosphoryl chloride (21.4 g) in dry dimethylformamide (40 ml), cooled in ice, was added portionwise to a solution of N-[2-[(2-furanylmethyl)thio]ethyl]-1H-isoindole-1,3(2H)-dione (21.4 g) in dry dimethylformamide (70 ml). After 5 hours at room temperature, the solution was poured into iced water (1.7 l). Isopropyl alcohol (150 ml) was added and after 18 hours the solid which separated was filtered and crystallised from ethyl acetate-ether to give the title compound (22.3 g) m.p. 76°-77°.

Workup

  1. customseparated
  2. filtrationwas filtered
  3. customcrystallised from ethyl acetate-ether

Sources & evidence

ORD record
ord-1eacc8d32d3c4d44976bc24771abbedd
Source dataset
uspto-grants-1983_08
Patent number
US04399294

Reaction notes

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