Bromine → HCID 22726737, compound

HRID 2085970Notes

Reaction equation

HRID 2085970 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:6]=1.[S-:19][C:20]#[N:21].[K+].BrBr>CO>[NH2:1][C:2]1[S:3][C:4]([S:19][C:20]#[N:21])=[C:5]([CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:6]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 22726757HCID 22726757, compound

Product 1

HCID 22726737HCID 22726737, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-amino-4-(2-t-butyloxycarbonylaminoethylthiomethyl)-1,3-thiazole (4.27 g, 14.8 mmol) and potassium thiocyanate (2.87 g, 29.5 mmol) in methanol (30 mL) cooled to 0° C. was added dropwise bromine (3.55 g, 0.022 mol) and stirring was continued for 45 min. Reaction mixture was partitioned between ethyl acetate and water. Organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford solid residue of title product in quantitative yield. Crude product was used in next step without further purification.

Workup

  1. customReaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. dry with materialOrganic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ffc5a495f2d49188f6849c706a8c6d9
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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