Bromine → HCID 178527224, compound

HRID 1906726Notes

Reaction equation

HRID 1906726 reaction equation
[C:1]1([SH:7]2(=[O:19])[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[CH:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]Br>C(Cl)(Cl)Cl>[Br:20][C:12]1[SH:7](=[O:19])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:8][CH:9]=[N:10][C:11]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178527219HCID 178527219, compound

Product 1

HCID 178527224HCID 178527224, compoundYield 160.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 4.5 g (16 mmole) of 1,5-diphenyl-1H-1,2,4-thiadiazine-1-oxide of Example 1 in 225 ml of chloroform was added over 20 minutes a solution of 2.8 g, (7.5 mmole) of bromine in 25 ml of chloroform. After the addition was complete, the mixture was stirred for 30 minutes before reducing to an oil which was subjected to flash chromatography (SiO2, petrol:chloroform 1:1) to obtain 4.2 g of (73%) 6-bromo-1,5-diphenyl-1H-1,2,4-thiadiazine-1-oxide melting at 135°-136° C. after crystallization from ethyl acetate/ether.

Workup

  1. additionAfter the addition

Sources & evidence

ORD record
ord-59e9993bc982442eb3adf9b672b9e5f2
Source dataset
uspto-grants-1987_03
Patent number
US04654338

Reaction notes

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