Methanol → HCID 22255988, compound

HRID 1611738Notes

Reaction equation

HRID 1611738 reaction equation
[OH:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:4][N:3]=1.[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>C1COCC1>[CH3:16][O:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([NH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[S:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 178510528HCID 178510528, compound

Product 1

HCID 22255988HCID 22255988, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxy-5-phenylamino-isothiazol-4-carbonitrile (2.82 g, 13 mmol), triphenylphosphine (4.04 g, 15.6 mmol), methanol (0.53 ml) in THF (25 ml) was added diethyl azadicarboxylate (DEAD, 2.46 ml, 15.6 mmol) at 0° C. The mixture was stirred at ambient temperature and evaporated to give a residue. The crude product was purified on silica gel (hexane/EtOAc, 1:1) to give a yellow powder (1.26 g, 42%).

Workup

  1. customevaporated
  2. customto give a residue
  3. customThe crude product was purified on silica gel (hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-0ee3cb2703a449039a63bbb2c25e6890
Source dataset
uspto-grants-2006_01
Patent number
US06989451B2

Reaction notes

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