Dimethylamine → HCID 20064736, compound

HRID 359258Notes

Reaction equation

HRID 359258 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[S:6][C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=1>C(OCC)C>[CH3:1][N:2]([CH3:3])[C:5]1[S:6][C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 20064736HCID 20064736, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a vessel containing 591 g of ethyl ether cooled in a dry ice-acetone bath was added 12.5 g of dimethylamine with stirring. Then, to a reaction vessel cooled in a dry-ice acetone bath there was placed 11.5 g of the previously-prepared dimethylamine-in-ether solution followed by addition of 5.79 g (23 mmol) of ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate in 20 ml of ethyl ether. A white precipitate formed immediately. The reaction mixture was stirred for 10 minutes and filtered. The ether filtrate was washed with 5% sodium hydroxide, dried over anhydrous calcium sulfate and concentrated under reduced pressure. The residual solid was treated with petroleum ether and filtered to provide 4.0 g of white solid product (m.p. 78°-79° C.) identified in Table I. ##STR18##

Workup

  1. temperaturecooled in a dry ice-acetone bath
  2. temperatureThen, to a reaction vessel cooled in a dry-ice acetone bath
  3. customA white precipitate formed immediately
  4. stirringThe reaction mixture was stirred for 10 minutes
  5. filtrationfiltered
  6. washThe ether filtrate was washed with 5% sodium hydroxide
  7. dry with materialdried over anhydrous calcium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionThe residual solid was treated with petroleum ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-87fbd5af450c4f3b85855a07426f9213
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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