Sulfuryl chloride → HCID 19758717, compound

HRID 1586639Notes

Reaction equation

HRID 1586639 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[NH:17][C:18]([CH2:20][C:21]([O:23][C:24]1[CH:45]=[CH:44][C:27]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:26][CH:25]=1)=[O:22])=[O:19]>ClCCl>[Cl:4][CH:20]([C:18](=[O:19])[NH:17][C:8]1[CH:9]=[C:10]([C:13]([F:15])([F:16])[F:14])[CH:11]=[CH:12][C:7]=1[Cl:6])[C:21]([O:23][C:24]1[CH:45]=[CH:44][C:27]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:26][CH:25]=1)=[O:22]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 19758719HCID 19758719, compound

Product 1

HCID 19758717HCID 19758717, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sulphuryl chloride (9.5 g, 70.2 m mol) in dichloromethane (15 ml) was slowly added to a solution of the 4-equivalent coupler from (d) (40 g, 70.2 m mol) in dichloromethane (250 ml). After stirring at room temperature for 20 h, the volatiles were evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (elutant 10% ethyl acetate in petrol (b.p. 60°-80° C.)) followed by recrystallization from methanol to give a white solid (25.2 g, 60%).

Workup

  1. customthe volatiles were evaporated under reduced pressure
  2. customThe crude product was purified by silica gel column chromatography (elutant 10% ethyl acetate in petrol (b.p. 60°-80° C.))
  3. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-fa50ea2aa45c497087e1dae9075510e2
Source dataset
uspto-grants-1993_06
Patent number
US05215878

Reaction notes

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