Hydrochloric Acid → HCID 86671863, compound

HRID 873552Notes

Reaction equation

HRID 873552 reaction equation
[CH3:1][N:2]([C:19]([F:35])([F:34])[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32]Cl)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)[S:3]([C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])(=[O:5])=[O:4].NC(N)=[S:38].[OH-].[Na+].Cl>C(C(C)=O)C.C(Cl)Cl.O>[CH3:1][N:2]([C:19]([F:35])([F:34])[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][SH:38])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)[S:3]([C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])(=[O:5])=[O:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 86671862HCID 86671862, compound

Product 1

HCID 86671863HCID 86671863, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 10.5 g (0.02 mol) of 4-(N-methylperfluorobutanesulfonamidomethyl)-4′-chloromethylbiphenyl, and 1.90 g (0.024 mol) thiourea in 100 mL methyl ethyl ketone was stirred and heated at reflux. The initial solution became cloudy and by 1 hr a white precipitate formed. The mixture was heated for 17 hr, cooled, and filtered. The product (8.2 g) was heated in 150 mL boiling ethanol under N2 and treated with 8 g (0.1 mol) 50% NaOH and heated for 20 hr. The resulting hazy solution was cooled, treated with 20 mL 10% HCl, and poured into 200 mL water to give a white solid. This was taken up in methylene chloride, dried over MgSO4, and stripped to 7.0 g of the desired product.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. customby 1 hr a white precipitate formed
  4. temperatureThe mixture was heated for 17 hr
  5. temperaturecooled
  6. filtrationfiltered
  7. temperatureThe product (8.2 g) was heated in 150 mL
  8. temperatureheated for 20 hr
  9. temperatureThe resulting hazy solution was cooled
  10. customto give a white solid
  11. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d29e30502de14265ae833c7b6427cb78
Source dataset
uspto-grants-2015_03
Patent number
US08975436B2

Reaction notes

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