Glycine → HCID 178419404, compound

HRID 1772707Notes

Reaction equation

HRID 1772707 reaction equation
[N:1]1[NH:2][N:3]=[C:4]([SH:6])[CH:5]=1.[Br:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].NCC(O)=O>CS(C)=O.CCOC(C)=O.[Cu]I>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:6][C:4]2[NH:3][N:2]=[N:1][CH:5]=2)=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 750GlycineHCID 115221-Bromo-4-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 178527740HCID 178527740, compound

Product 1

HCID 178419404HCID 178419404, compoundYield 40.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2H-1,2,3-triazole-4-thiol (870 mg, 7.10 mmol), 1-bromo-4-iodobenzene (1.00 g, 3.50 mmol), K3PO4 (1.90 g, 8.80 mmol), CuI (67.0 mg, 0.350 mmol) and glycine (132.7 mg, 1.80 mmol) in DMSO (10 mL) was heated to 110° C. for 3 days. The reaction mixture was cooled to rt, diluted with EtOAc (500 mL) and washed with water (2×400 mL) followed by brine (400 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 360 mg of compound 63a as a white solid. Mass Spectrum LCMS, ESI (pos.) Calcd. for C8H6BrN3S: 256.1 [M+H]. found 256.1.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. washwashed with water (2×400 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c28bfff3c3644b2aaf621095a431868
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…