Thionyl Chloride → 2-Phenylbenzenesulfonyl isothiocyanate

HRID 637870

Reaction equation

HRID 637870 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([N:10]=[C:11]([S-])[S-:12])(=[O:9])=[O:8].[K+].[K+].S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:14]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[S:7]([N:10]=[C:11]=[S:12])(=[O:9])=[O:8])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13422022HCID 13422022, compound

Product 1

HCID 134220272-Phenylbenzenesulfonyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

77 g of potassium N-(2-biphenylylsulfonyl)carbonimidodithioate prepared in accordance with Example 2 was suspended in 100 ml of toluene, and 37 ml of thionyl chloride was added to the suspension at 0° to 10° C. over the course of 1 hour. After the addition, the mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. Distillation at reduced pressure gave 2-phenylbenzenesulfonyl isothiocyanate. On the other hand, 12.3 g of 2-amino-4,6-dimethylpyrimidine was suspended in 300 ml of dry toluene, and 27.5 g of 2-phenylbenzenesulfonyl isothiocyanate prepared as above was added. The mixture was heated under reduced pressure for 8 hours. After cooling, the resulting white precipitate was collected by filtration, and recrystallized from ethanol to give 31 g of the desired 1-(2-biphenylsulfonyl)3-(4,6-dimethylpyrimidin-2-yl)thiourea of the following formula, mp. 203°-204° C.: ##STR20##

Workup

  1. additionAfter the addition
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. distillationDistillation at reduced pressure

Sources & evidence

ORD record
ord-f7288056c5d74c808da8f35e1016e01b
Source dataset
uspto-grants-1985_12
Patent number
US04559079

Linked notes

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