Diglyme → HCID 14851833, compound

HRID 1032745Notes

Reaction equation

HRID 1032745 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=O)[CH2:10][N:9]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22].C(=O)(O)[O-].[Na+].COCCOCCOC>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[S:22])[CH2:10][N:9]=1

Participants

6

Reactant 4

HCID 8150DiglymeHCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 3082318Ro 7-9749

Product 1

HCID 14851833HCID 14851833, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 31 g (0.08 mol) of 1,3-dihydro-5-(2-fluoro phenyl)-7-iodo-1,4-benzodiazepin-2(2H)-one [ref. G. F. Field and L. H. Sternbaoh, Swiss patents Nos. 561,706; May 1975; and 562,222; April 1975], 20 g (0.09 mol) of phosphorus pentasulfide, 20 g of sodium bicarbonate and 300 ml of diglyme was stirred and heated to 80°-85° C. for 3 hours. The reaction mixture was then poured onto ice and diluted with water. After stirring for 30 minutes, the solid yellow product was filtered off, washed with water, 2-propanol and little ether. It was sucked dry in the funnel and further dried in vacuum to leave 26 g (80%) of 1,3-dihydro-5-(2-fluorophenyl)-7-iodo-1,4-benzodiazepine-2(2H)-thione which was further transformed as described below. Pure material was obtained by recrystallization from tetrahydrofuran/ethanol and had m.p. 242°-244° C.

Workup

  1. temperatureheated to 80°-85° C. for 3 hours
  2. additionThe reaction mixture was then poured onto ice
  3. stirringAfter stirring for 30 minutes
  4. filtrationthe solid yellow product was filtered off
  5. washwashed with water, 2-propanol and little ether
  6. customIt was sucked dry in the funnel
  7. customfurther dried in vacuum

Sources & evidence

ORD record
ord-cc2d4be6e56748eab91641bde5eb3d7e
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

Loading…