Tert-Butylamine → HCID 15682570, compound

HRID 1590001Notes

Reaction equation

HRID 1590001 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]1([C:12]2[S:16][N:15]=[C:14]3[C:17]([O:19][C:20](=[O:21])[C:13]=23)=[O:18])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[C:1]([NH:5][C:17]([C:14]1[C:13]([C:20]([OH:21])=[O:19])=[C:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[S:16][N:15]=1)=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 15682569HCID 15682569, compound

Product 1

HCID 15682570HCID 15682570, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With ice cooling, 0.64 g (8.8 mmol) of tert-butylamine was dripped into 2.0 g (8.7 mmol) of 5-phenyl-isothiazole-3,4-dicarboxylic anhydride in 10 ml of dichloromethane, and the whole was stirred for 3 hours at room temperature. The solution was when evaporated down, 25 ml of water was added, and the solution was acidified to a pH of 2 with 6N HCl and extracted three times, each time with 30 ml of ethyl acetate. The organic phase was washed with 20 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated down. The residue was chromatographed on silica gel (developer: ethanol/toluene 2:3). Yield: 49%.

Workup

  1. customevaporated down
  2. addition25 ml of water was added
  3. extractionextracted three times
  4. washThe organic phase was washed with 20 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated down
  7. customThe residue was chromatographed on silica gel (developer: ethanol/toluene 2:3)

Sources & evidence

ORD record
ord-2d7f764efa744ef5b3013e965a601a59
Source dataset
uspto-grants-1993_04
Patent number
US05201932

Reaction notes

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