Carbon Tetrachloride → 2-Acetylamino-5-[2,2-dichloro-1-(ethoxycarbonyl-hydrazono)-ethyl]-4-trifluoromethyl-benzoic acid methyl ester

HRID 906628Notes

Reaction equation

HRID 906628 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([C:10](=[N:12][NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])C)[C:7]([C:19]([F:22])([F:21])[F:20])=[CH:6][C:5]=1[NH:23][C:24](=[O:26])[CH3:25].ClN1C(=O)CCC1=O.[C:36]([Cl:40])(Cl)(Cl)[Cl:37]>>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([C:10](=[N:12][NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:36]([Cl:40])[Cl:37])[C:7]([C:19]([F:22])([F:21])[F:20])=[CH:6][C:5]=1[NH:23][C:24](=[O:26])[CH3:25]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 31398ChlorosuccinimideHCID 866210242-Acetylamino-5-[1-(ethoxycarbonyl-hydrazono)-ethyl]-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 866210252-Acetylamino-5-[2,2-dichloro-1-(ethoxycarbonyl-hydrazono)-ethyl]-4-trifluoromethyl-benzoic acid methyl ester

Conditions

Temperature
110 °C

Procedure

To a solution of 2-acetylamino-5-[1-(ethoxycarbonyl-hydrazono)-ethyl]-4-trifluoromethyl-benzoic acid methyl ester (1.1 g, 2.83 mmol) in CCl4 (18 mL) was added N-chlorosuccinimide (770 mg, 5.65 mmol). The reaction vessel was flushed with argon and the reaction mixture was heated to 110° C. for 38 h. After cooling to r.t., the mixture was filtered and the filtrate was concentrated in vacuo to provide the intermediate 2-acetylamino-5-[2,2-dichloro-1-(ethoxycarbonyl-hydrazono)-ethyl]-4-trifluoromethyl-benzoic acid methyl ester which was used directly in the next step. (API-ES: m/z 455.9 [M−H]−, rt 5.04 min).

Workup

  1. customThe reaction vessel was flushed with argon
  2. temperatureAfter cooling to r.t.
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3f2886228e174d4fb83ec46e5c1206cc
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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