Bromoacetyl bromide → HCID 22452250, compound

HRID 2185807Notes

Reaction equation

HRID 2185807 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].[Br:15][CH2:16][C:17](Br)=[O:18]>C(Cl)(Cl)Cl>[Br:15][CH2:16][C:17]([NH:7][C:6]1[CH:8]=[CH:9][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1)=[O:18]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 660384-(Methylthio)anilineHCID 516892Sodium Bicarbonate

Product 1

HCID 22452250HCID 22452250, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-(methylthio)aniline (200 mg, 1.44 mmol) in chloroform (2 ml), a saturated aqueous solution of sodium hydrogencarbonate (2 ml) was added, followed by the dropwise addition of a solution of bromoacetyl bromide (300 mg, 1.49 mmol) in chloroform (2 ml) under ice cooling. The mixture was then stirred for 1 hour. The chloroform layer was separated, washed successively with 2N hydrochloric acid (10 ml) and brine (10 ml), and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, whereby the title compound (356 mg, 95.3%) was obtained as pale brown crystals.

Workup

  1. customThe chloroform layer was separated
  2. washwashed successively with 2N hydrochloric acid (10 ml) and brine (10 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure, whereby the title compound (356 mg, 95.3%)
  5. customwas obtained as pale brown crystals

Sources & evidence

ORD record
ord-a5a993867ddc4f869eed2b281b2d9eaf
Source dataset
uspto-grants-2002_06
Patent number
US06403586B1

Reaction notes

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