2,4,5-Trichlorophenol → HCID 68937494, compound

HRID 2199729Notes

Reaction equation

HRID 2199729 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17]OS(C1C=CC(C)=CC=1)(=O)=O)=[CH:12][CH:11]=[CH:10][C:9]=2[C:29]1[CH:34]=[CH:33][C:32]([C:35]([O:37]C)=[O:36])=[CH:31][C:30]=1[CH3:39])=[O:5])C.[Cl:40][C:41]1[CH:46]=[C:45]([Cl:47])[C:44]([Cl:48])=[CH:43][C:42]=1[OH:49].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[C:35]([C:32]1[CH:33]=[CH:34][C:29]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:8]=2[NH:7][C:6]([C:4]([OH:5])=[O:3])=[C:14]3[CH2:15][CH2:16][CH2:17][O:49][C:42]2[CH:43]=[C:44]([Cl:48])[C:45]([Cl:47])=[CH:46][C:41]=2[Cl:40])=[C:30]([CH3:39])[CH:31]=1)([OH:37])=[O:36]

Participants

6

Reactant 3

HCID 72712,4,5-TrichlorophenolHCID 10796Cesium carbonateHCID 87630457HCID 87630457, compound

Product 1

HCID 68937494HCID 68937494, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of EXAMPLE 127C (60 mg) in DMF (1 mL) was added 2,4,5-trichlorophenol (43 mg) and Cs2CO3 (500 mg). The mixture was stirred at room temperature overnight, diluted with ethyl acetate (150 mL), and washed with water and brine. After drying over Na2SO4, the combined organic layers were concentrated, and the concentrate was saponified with LiOH as described in EXAMPLE 65B. 1H NMR (300 MHz, DMSO-d6) δ 12.92 (m, 1H), 10.88 (s, 1H), 7.89 (s, 1H), 7.82 (m, 2H), 7.38 (s, 1H), 7.32 (d, 1H), 7.10 (m, 2H), 4.13 (t, 2H), 3.25 (t, 2H), 2.13 (m, 2H), 2.10 (s, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialAfter drying over Na2SO4
  3. concentrationthe combined organic layers were concentrated

Sources & evidence

ORD record
ord-08896b6276724fd79955c92c5c50012c
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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