Chlorosulfonic acid → HCID 59465632, compound

HRID 1876631Notes

Reaction equation

HRID 1876631 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[Cl:19][S:20](O)(=[O:22])=[O:21]>>[F:18][C:2]([F:1])([F:17])[C:3]([N:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([S:20]([Cl:19])(=[O:22])=[O:21])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 839837HCID 839837, compound

Product 1

HCID 59465632HCID 59465632, compoundYield 72%

Conditions

Temperature
155 °C

Procedure

A mixture of 2,2,2-trifluoro-1-(4-phenylpiperazin-1-yl)ethanone (1.0 g, 3.9 mmol) and chlorosulfonic acid (6 mL) was heated at 155° C. for 15 min. After cooling to RT, the mixture was poured into ice water and extracted with EtOAc. The organic layer was concentrated and purified via silica gel chromatography using 7/3 hexanes/EtOAc to obtain 4-(4-(2,2,2-trifluoroacetyl)piperazin-1-yl)benzene-1-sulfonyl chloride as a yellow solid (1.0 g, 72%). 1H NMR (400 MHz, CDCl3) δ 7.93-7.89 (m, 2H), 6.96-6.92 (m, 2H), 3.88 (t, J=5.3 Hz, 2H), 3.83 (t, J=5.1 Hz, 2H), 3.55-3.52 (m, 4H).

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated
  4. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-7b5c00f99b944a78bc0836656811a087
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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