Hydrochloric Acid → 2-Chloro-4-fluoro-N-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-benzamide

HRID 60567Notes

Reaction equation

HRID 60567 reaction equation
Cl.[NH2:2][C:3]1[CH:12]=[CH:11][C:6]2[CH2:7][O:8][B:9]([OH:10])[C:5]=2[CH:4]=1.C(N(CC)CC)C.[Cl:20][C:21]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].Cl>ClCCl>[Cl:20][C:21]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:22]=1[C:23]([NH:2][C:3]1[CH:12]=[CH:11][C:6]2[CH2:7][O:8][B:9]([OH:10])[C:5]=2[CH:4]=1)=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 441187306-Amino-2,1-benzoxaborol-1(3H)-ol--hydrogen chloride (1/1)

Product 1

HCID 461940362-Chloro-4-fluoro-N-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-benzamideYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250 ml round bottom flask was charged with a mixture of 6-amino-1-hydroxy-2,1-benzoxaborolane hydrochloride (1 g, 5.4 mmol, 1 eq), triethylamine (2.3 ml, 16.2 mmol, 3 eq) and dichloromethane (100 ml). 2-Chloro-4-fluorobenzoyl chloride (1.14 g, 5.9 mmol, 1.1 eq) was added, and the reaction mixture was allowed to stir at room temperature overnight. Aqueous hydrochloric acid (1 M, 50 ml) was added to the mixture and the suspension was vigorously mixed. The resulting white precipitate was then collected by vacuum filtration and dried under vacuum. LCMS (m/e) 306 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.96 (s, 2H) 7.29-7.45 (m, 2H) 7.59 (dd, J=9.0, 2.3 Hz, 1H) 7.63-7.78 (m, 2H) 8.15 (d, J=1.8 Hz, 1H) 9.25 (s, 1H) 10.53 (s, 1H). Amount Obtained: 1.1 g, 67% yield.

Workup

  1. additionthe suspension was vigorously mixed
  2. filtrationThe resulting white precipitate was then collected by vacuum filtration
  3. customdried under vacuum
  4. customAmount Obtained

Sources & evidence

ORD record
ord-7a77d63464644957a3b7f87b43c290bc
Source dataset
uspto-grants-2016_09
Patent number
US09440994B2

Reaction notes

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