Potassium Carbonate → HCID 22726757, compound

HRID 2085969Notes

Reaction equation

HRID 2085969 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7]Cl)[N:6]=1.[C:9]([O:13][C:14]([NH:16][CH2:17][CH2:18][SH:19])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:19][CH2:18][CH2:17][NH:16][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 732294-Chloromethylthiazol-2-ylamineHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiol

Product 1

HCID 22726757HCID 22726757, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-4-chloromethyl-1,3-thiazole (16.2 g, 0.108 mol) in dimethylformamide (80 mL) was added 2-t-butyloxycarbonylaminoethanethiol (28.9 g, 0.163 mol) followed by potassium carbonate (45 g, 0.326 mol). After 1 hour of vigorous stirring reaction mixture was partitioned between ethyl acetate and water. Organic layer was thoroughly washed with water, dried over sodium sulfate and concentrated under reduced pressure. Flash column chromatography of the oily residue (2% methanol in methylene chloride) afforded oily product (20.0 g). 1H NMR (CDCl3) δ 1.42 (s, 9H), 2.65 (m, 2H), 3.35 (m, 2H), 3.80 (s, 2H), 2.65 (m, 2H), 5.00 (s, 1H).

Workup

  1. customreaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. washOrganic layer was thoroughly washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc0a8ef1fb094a6da9fdd727ff988450
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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