Sodium Hydroxide → 4-[4-(3-Chloro-4-fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid

HRID 1519274Notes

Reaction equation

HRID 1519274 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[C:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])=[CH:9][CH:10]=[C:11]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=3)[N:17]=2)[CH:12]=1)=[O:6]>O.O1CCOCC1>[Cl:25][C:20]1[CH:19]=[C:18]([C:16]2[N:17]=[C:13]([C:11]3[CH:12]=[C:7]([C:5]([OH:6])=[O:4])[C:8]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[N+:32]([O-:34])=[O:33])=[CH:9][CH:10]=3)[S:14][CH:15]=2)[CH:23]=[CH:22][C:21]=1[F:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 866798424-[4-(3-Chloro-4-fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid methyl ester

Product 1

HCID 715366284-[4-(3-Chloro-4-fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acidYield 61.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydroxide (100 mg, 2.5 mmol) was added to a suspension of 4-[4-(3-chloro-4-fluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid methyl ester (100 mg) in a mixture of water (2 mL) and dioxane (4 mL). The reaction mixture was stirred at 50° C. for 2 h. An additional portion of water (2 mL) was added and the reaction mixture was stirred at 50° C. for a further 2 h. The reaction mixture was evaporated to dryness and water (5 mL) was added. The mixture was filtered and the filtrate was made acidic to pH 3-4 by the addition of concentrated HCl. The precipitate was collected by filtration and dried to give 4-[4-(3-chloro-4-fluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (60 mg, 41% for two steps). 1H NMR (300 MHz, DMSO-d6) δ 13.18 (br s, 1H), 8.56 (s, 1H), 8.39 (s, 1H), 8.27 (d, J=8.3 Hz, 1H), 8.08-8.16 (m, 2H), 7.79 (t, J=7.4 Hz, 1H), 7.66 (t, J=7.9 Hz, 1H), 7.41-7.58 (m, 3H).

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for a further 2 h
  2. customThe reaction mixture was evaporated to dryness and water (5 mL)
  3. additionwas added
  4. filtrationThe mixture was filtered
  5. additionthe filtrate was made acidic to pH 3-4 by the addition of concentrated HCl
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-8f2bbfd22f2f4a7d9e5fda90c312c697
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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