Hydrogen Bromide → HCID 20300309, compound

HRID 2083090Notes

Reaction equation

HRID 2083090 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[C:13](=[O:14])[C:12](=[O:15])[NH:11][C:10]1=[S:16].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Br:23].Br>CS(C)=O.CCCCCC>[Br:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:11]1[C:12](=[O:15])[C:13](=[O:14])[N:9]([CH3:8])[C:10]1=[S:16]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 81001,5-DibromopentaneHCID 8471TriethylamineHCID 203003261-Methyl-2-sulfanylideneimidazolidine-4,5-dione

Product 1

HCID 20300309HCID 20300309, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Procedure

Triethylamine (84 ml, 0.60 mole) was added dropwise over a period of 6 hours to a stirred solution of 1-methyl-2-thioxo-4,5-imidazolidinedione (88 g, 0.61 mole) and 1,5-dibromopentane (264 g, 1.20 mole) in dimethylsulphoxide (650 ml) at room temperature. The mixture was allowed to stand overnight and then poured into ice water (3 liters) containing concentrated hydrobromic acid (1 ml). The mixture was extracted with chloroform and the extracts were washed with water, dried over magnesium sulphate and evaporated to give an oil which was treated with hexane to give yellow crystals of 1-(5-bromopentyl)-3-methyl-2-thioxo-4,5-imidazolidinedione (82.3 g), m.p. 48°-50°.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washthe extracts were washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customto give an oil which

Sources & evidence

ORD record
ord-4c3c951bf6054e4bba261877c0f3890d
Source dataset
uspto-grants-1978_04
Patent number
US04084001

Reaction notes

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