Bromine → HCID 15580980, compound

HRID 443892Notes

Reaction equation

HRID 443892 reaction equation
O[CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[S:6].BrBr>ClC(Cl)(Cl)Cl>[C:14]1([CH:2]2[N:7]3[C:5]([S:6][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=43)=[N:4][CH2:3]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 2873543HCID 2873543, compound

Product 1

HCID 15580980HCID 15580980, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 50 parts of N-(2-hydroxy-2-phenylethyl)N'-phenylthiourea, 30 parts of bromine and 800 parts tetrachloromethane is stirred and refluxed for 2 hours. The reaction mixture is evaporated. From the residue, the free base is liberated in the conventional manner with ammonium hydroxide and extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is suspended in boiling 4-methyl-2-pentanone. The product is filtered off and stirred in a diluted sodium hydroxide solution. The product is extracted with 4-methyl-2-pentanone. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from acetonitrile. The product is filtered off and dried, yielding 10 parts (22%) of 2,3-dihydro-3-phenylimidazo[2,1-b]benzothiazole; mp. 131.7° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe reaction mixture is evaporated
  3. extractionextracted with trichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe product is filtered off
  8. stirringstirred in a diluted sodium hydroxide solution
  9. extractionThe product is extracted with 4-methyl-2-pentanone
  10. washThe extract is washed with water
  11. customdried
  12. filtrationfiltered
  13. customevaporated
  14. customThe residue is crystallized from acetonitrile
  15. filtrationThe product is filtered off
  16. customdried

Sources & evidence

ORD record
ord-1f081ba92a65461fa92fb52ee9915208
Source dataset
uspto-grants-1981_04
Patent number
US04262004

Reaction notes

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