Triethylamine → HCID 58495582, compound

HRID 1191028Notes

Reaction equation

HRID 1191028 reaction equation
[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7](Cl)=[O:8].[NH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7]([NH:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 133964-AminobenzonitrileHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

Product 1

HCID 58495582HCID 58495582, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Add a solution of 2,2,3,3-tetramethyl-cyclopropane-carbonyl chloride (5 g, 31.1 mmol) in anhydrous DCM to a mixture of 4-aminobenzonitrile (3.34 g, 28.3 mmol) and triethylamine (4.3 mL, 31 mmol) in anhydrous DCM (20 mL) at 0° C. After stirring at 0° C. for 20 min, warm the mixture to room temperature and stir overnight. Partition the reaction mixture between DCM (500 mL) and water (250 mL) and extract the aqueous phase with DCM (250 mL). Wash combined organic extracts with water (3×250 mL), dry over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 over 36 min; 1:0 to 3:1 gradient over 36 min; 3:1 to 1:1 gradient over 71 min; 50 mL/min) to obtain the desired intermediate as a solid (2.31 g, 34%). MS (ES+) m/z: 243.2 (M+H)+.

Workup

  1. temperaturewarm the mixture to room temperature
  2. stirringstir overnight
  3. customPartition the reaction mixture between DCM (500 mL) and water (250 mL)
  4. extractionextract the aqueous phase with DCM (250 mL)
  5. washWash
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 over 36 min; 1:0 to 3:1 gradient over 36 min; 3:1 to 1:1 gradient over 71 min; 50 mL/min)

Sources & evidence

ORD record
ord-38ff63d4957f40a39668010441315185
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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