Trifluoroacetic acid → HCID 67452000, compound

HRID 716714Notes

Reaction equation

HRID 716714 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-2 H-pyran-4-yl)-1,3-oxazole (7.45 g) as a white solid. MS: M+H=296. H′NMR (400 MHz, CDCl3) δ: 7.27 (d, J=10.3 Hz, 2 H), 7.26 (s, 1 H), 7.17 (d, J=10.3 Hz, 2 H), 4.01 (dt, J=33, 12.2 Hz, 2 H), 3.51 (td, J=3.7, 12.2 Hz, 2 H), 3.10-3.00 (m, 1 H), 2.04-1.85 (m, 4 H).

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-183668da65724207b2f943fa76feea3b
Source dataset
uspto-grants-2015_11
Patent number
US09193697B2

Reaction notes

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