Sodium Hydroxide → 1-(2,5-Dibromophenyl)thiourea

HRID 2068672Notes

Reaction equation

HRID 2068672 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=1[Br:20])=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1>[Br:20][C:14]1[CH:15]=[CH:16][C:17]([Br:19])=[CH:18][C:13]=1[NH:12][C:10]([NH2:9])=[S:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 596030861-Benzoyl-3-(2,5-dibromo-phenyl)-thiourea

Product 1

HCID 532116341-(2,5-Dibromophenyl)thioureaYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
62.5 °C

Procedure

To a solution of 1-benzoyl-3-(2,5-dibromo-phenyl)-thiourea II (3.90 g, 11.8 mmol) in THF (80 mL) was added NaOH solution (1.13 g in 20 mL H2O) at room temperature. The reaction mixture was then heated up to 60-65° C. overnight. After completion of the reaction (TLC monitoring) THF was distilled off followed by addition of water, and extracted with ethyl acetate (2×50 mL). The combined organic layers were combined and dried over anhydrous Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude residue was washed with mixture of hexane and diethyl ether (95:5) and dried under high vacuum to obtain the desired product as pale-yellow solid (2.5 g, 86%). 1H NMR (DMSO-d6, 400 MHz): δ 7.35 (dd, J=8.80 and 2.80 Hz, 1H), 7.48 (br s, 1H), 7.60 (d, J=8.40 Hz, 1H), 7.87 (d, J=2.40 Hz, 1H), 8.0 (br s, 1H) and 9.33 (br s, 1H). MS: 308.98 (M+H+).

Workup

  1. distillationwas distilled off
  2. additionfollowed by addition of water
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. washThe crude residue was washed with mixture of hexane and diethyl ether (95:5)
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-f8d1ae780a79460ab1b65e4051323e13
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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