Diisopropylamine → 79505-01-4

HRID 1779426Notes

Reaction equation

HRID 1779426 reaction equation
C([Li])CCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(NC(C)C)(C)C.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24]([OH:26])=[O:25].C1C[O:30][CH2:29]C1>O.C(#N)C1C=CC=CC=1>[C:8]1([C:29]([C:23]2[S:19][C:20]([C:24]([OH:26])=[O:25])=[CH:21][CH:22]=2)=[O:30])[CH:7]=[CH:6][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 8058HexaneHCID 107002-Thiophenecarboxylic acidHCID 178418339Butyllithium

Product 1

HCID 1082345879505-01-4

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7505BenzonitrileSolvent

Conditions

Temperature
-70 °C

Procedure

A 1.6M solution of n-butyllithium in n-hexane (51.0 ml, 81.3 mmol) is added dropwise to diisopropylamine (11.6 ml, 82.2 mmol) in 150 ml of absolute THF at -70° C. After stirring at -70° C. for 15 minutes, thiophene-2-carboxylic acid (5.00 g, 39.0 mmol) is added and the mixture is held at -70° C. After 45 minutes benzonitrile (5.0 ml, 49 nunol) is added dropwise and the mixture is stirred at -70° C. for 90 minutes. After equilibration to room temperature, the reaction mixture is poured into 200 ml of water and subjected to extraction with 200 ml of ether, and this organic phase is discarded. The aqueous phase is adjusted to a pH of 2 using a 6N HCl solution and is subjected to extraction with 2×200 ml of ether. The combined organic phases are dried over magnesium sulfate and the solvent is distilled off. The residue is suspended in 50 ml of 6N HCl solution and the suspension is heated at 80° C. for one hour. The precipitated crystals are filtered off and dried under vacuum overnight.

Workup

  1. customis held at -70° C
  2. stirringthe mixture is stirred at -70° C. for 90 minutes
  3. extractionsubjected to extraction with 200 ml of ether
  4. extractionis subjected to extraction with 2×200 ml of ether
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. distillationthe solvent is distilled off
  7. temperaturethe suspension is heated at 80° C. for one hour
  8. filtrationThe precipitated crystals are filtered off
  9. customdried under vacuum overnight

Sources & evidence

ORD record
ord-6eb19be5923544a9b61c15ba85dcdd85
Source dataset
uspto-grants-1997_05
Patent number
US05627198

Reaction notes

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