Trifluoroacetic acid → HCID 67452000, compound

HRID 1519230Notes

Reaction equation

HRID 1519230 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][NH:11][C:12]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.C1C(=O)N(Cl)C(=O)C1.C(O)(C(F)(F)F)=O>ClC1C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31398ChlorosuccinimideHCID 51201387HCID 51201387, compound

Product 1

HCID 67452000HCID 67452000, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Procedure

To a solution of N-{2-[(4-chlorophenyl)sulfanyl]ethyl}tetrahydro-2H-pyran-4-carboxamide (9.48 g, 31.6 mmol) in chlorobenzene (316 ml) was added NCS (8.44 g, 63.2 mmol) by portions and the reaction mixture was stirred at RT for 1 h. TFA (1.218 ml, 15.81 mmol) was added and the reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with DCM, washed with aq NaHCO3, dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (silica 2×330 g, 0 to 50% EtOAc in hexane), to give 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole (7.45 g) as a white solid. MS: M+H=296. H1NMR (400 MHz, CDCl3) δ: 7.27 (d, 0.1=10.3 Hz, 2H), 7.26 (s, 1H), 7.17 (d, J=10.3 Hz, 2H), 4.01 (dt, J=12.2 Hz, 3.7 Hz, 2H), 3.51 (td, J=12.2 Hz, 3.7 Hz, 2H), 3.10-3.00 (m, 1H), 2.04-1.85 (m, 4H).

Workup

  1. stirringthe reaction mixture was stirred at RT for 16 h
  2. washwashed with aq NaHCO3
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography (silica 2×330 g, 0 to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-08a44d52dd754671b27601b42f70a870
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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