Triethylamine → [3-{[(Dimethylamino)carbonothioyl]oxy}-5-(trifluoromethyl)phenyl]acetic acid

HRID 1686438Notes

Reaction equation

HRID 1686438 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:16][N:17]([CH3:21])[C:18](Cl)=[S:19].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.O1CCOCC1.O>[CH3:16][N:17]([CH3:21])[C:18]([O:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1)=[S:19]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 690656243-Hydroxy-5-(trifluoromethyl)phenylacetic acid

Product 1

HCID 86625039[3-{[(Dimethylamino)carbonothioyl]oxy}-5-(trifluoromethyl)phenyl]acetic acid

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from example 25 step (iv) (0.5 g), dimethylthiocarbamoyl chloride (0.32 ml), DMAP (0.026 g) and triethylamine (0.60 ml) in dry dioxane (10 ml) were stirred at 100° C. for 15 h. The mixture was diluted with water, extracted with ethyl acetate, dried (MgSO4) and evaporated under reduced pressure to an oil. The oil was purified by flash column chromatography (eluent ether) to give the subtitle compound (0.52 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure to an oil
  4. customThe oil was purified by flash column chromatography (eluent ether)

Sources & evidence

ORD record
ord-d2d965d649a74f638088da9a869bd329
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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