Hydrochloric Acid → HCID 86624775, compound

HRID 2052756Notes

Reaction equation

HRID 2052756 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23](=[N:28][OH:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)=[CH:8][CH:7]=1)=[N:4][OH:5].N1C(C)=CC=CC=1C.Cl[CH2:41][CH2:42][S:43](Cl)(=[O:45])=[O:44].Cl>C(Cl)Cl>[CH:42]([S:43]([OH:45])(=[O:5])=[O:44])=[CH2:41].[F:1][C:2]([F:30])([F:31])[C:3]([C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23](=[N:28][O:29][S:43]([CH:42]=[CH2:41])(=[O:45])=[O:44])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)=[CH:10][CH:11]=1)=[N:4][OH:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 74062449HCID 74062449, compound

Product 1

HCID 86624775HCID 86624775, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In 30 mL of CH2Cl2 are dissolved 3.0 g (6.66 mmol) of 2,2,2-Trifluoro-1-(4-{3-[4-(2,2,2-trifluoro-1-hydroxyimino-ethyl)-phenoxy]-propoxy}-phenyl)-ethanone oxime, which is prepared according to the method described in GB 2348644, and the solution is cooled in an ice-bath. To the solution are added successively 2,6-lutidine (3.5 mL, 30.0 mmol) and 2-chloroethanesulfonyl chloride (1.55 mL, 14.7 mmol), and the reaction solution is stirred at 0° C. for 1 h and at room temperature for 2.5 h. Then, it is poured into 1N HCl. The crude product is extracted with CH2Cl2, washed with 1N HCl, dried over MgSO4 and concentrated. The residue is purified by recrystallizaffon from methanol to afford the product as a beige solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.32 (m, 2H), 4.23 (t, 4H), 6.32 (d, 2H), 6.61 (d, 2H), 6.72 (dd, 2H), 7.00 (d, 4H), 7.50 (d, 4H). mp. 84-88° C.

Workup

  1. customis prepared
  2. temperaturethe solution is cooled in an ice-bath
  3. extractionThe crude product is extracted with CH2Cl2
  4. washwashed with 1N HCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by recrystallizaffon from methanol

Sources & evidence

ORD record
ord-407fde0e2aef4c45b8e72d854739397f
Source dataset
uspto-grants-2008_02
Patent number
US07326511B2

Reaction notes

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