Sodium Chloride → HCID 21475339, compound

HRID 2294635Notes

Reaction equation

HRID 2294635 reaction equation
CS(Cl)(=O)=O.O[CH:7]1[O:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:8]1=[O:22].C(N)C=C.[Cl-:27].[Na+]>C(OCC)C.ClCCl.C(N(CC)CC)C>[Cl:27][CH:7]1[O:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:8]1=[O:22]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 7853AllylamineHCID 31297Methanesulfonyl chlorideHCID 11118371HCID 11118371, compound

Product 1

HCID 21475339HCID 21475339, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent3×HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Methanesulphonyl chloride (0.9 g) dissolved in diethylether (2 ml) was added to a stirred solution of 5-hydroxy-3-(3-trifluoromethylphenyl)oxazolidin4-one (1.0 g, Example 2, Step 4) in dichloromethane (6 ml). Triethylamine (0.8 g) dissolved in ether (2 ml) was added and the mixture allowed to exotherm to 35° C. After 2 hours the mixture was cooled in an ice-water bath and a solution of allylamine (0.92 g) in ether (2 ml) added dropwise. After 1 hour the mixture was treated with aqueous sodium chloride (20 ml), extracted with ether (3×80 ml), the extract dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the crude product as a yellow gum (1.3 g). 1H NMR (CDCl3): δ 3.49(2 H,d); 5.13(1 H,dd); 5.21 (1 H,s); 5.3(1 H,m); 5.44(1 H,d); 5.48(1H,dd); 5.9(1 H,m); 7.5-7.8(4 H,m).

Workup

  1. additionwas added
  2. customto exotherm to 35° C
  3. temperatureAfter 2 hours the mixture was cooled in an ice-water bath
  4. extractionextracted with ether (3×80 ml)
  5. dry with materialthe extract dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2fd2c16be7f4f058720aed3158ecd21
Source dataset
uspto-grants-1997_11
Patent number
US05688962

Reaction notes

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