Isopropylamine → HCID 86736808, compound

HRID 1448693Notes

Reaction equation

HRID 1448693 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[C:13]([C:14](Cl)=[O:15])=[CH:12][S:11][N:10]=2)[CH:4]=1.[CH:19]([NH2:22])([CH3:21])[CH3:20]>C1COCC1>[CH:19]([NH:22][C:14]([C:13]1[C:9]([C:5]2[CH:4]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:8]=[CH:7][CH:6]=2)=[N:10][S:11][CH:12]=1)=[O:15])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 23465058HCID 23465058, compound

Product 1

HCID 86736808HCID 86736808, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g (0.0034 mol) of 3-(α,α,α-trifluoro-m-tolyl)-4-isothiazolecarbonyl chloride and 20 cc of THF was added 0.45 g (2.1 equivalents) of isopropylamine. The reaction mixture was heated on a steam bath for 20 minutes. The isopropylamine hydrochloride was filtered off and the filtrate was concentrated to a solid. The solid was washed with H2O, dissolved in THF, dried (CaSO4), and concentrated under vacuum to give 0.94 g of solid. The solid was recrystallized from EtOAc/hexane to give 0.4 g white solid, m.p. 166°-167°. The filtrates gave another 0.3 g of white solid, m.p. 166.5°-168°. (Total yield=88%).

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 20 minutes
  2. filtrationThe isopropylamine hydrochloride was filtered off
  3. concentrationthe filtrate was concentrated to a solid
  4. washThe solid was washed with H2O
  5. dissolutiondissolved in THF
  6. dry with materialdried (CaSO4)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7bdff4aa114041438874db3403372bb5
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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