Hydrochloric Acid → HCID 53404021, compound

HRID 1619151Notes

Reaction equation

HRID 1619151 reaction equation
C[Si]([N-:5][Si](C)(C)C)(C)C.[Li+].[I:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:15]#[N:16].O.Cl>O1CCCC1>[I:11][C:12]1[CH:13]=[C:14]([C:15](=[NH:5])[NH2:16])[CH:17]=[CH:18][C:19]=1[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 121296213-Iodo-4-methylbenzonitrile

Product 1

HCID 53404021HCID 53404021, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 9.9 mL, 9.9 mmol) was added dropwise over 2 minutes to a cooled (10° C.) solution of 3-iodo-4-methylbenzonitrile (preparation 51a, 2.00 g, 8.2 mmol) in tetrahydrofuran (10 mL). After 1.5 hours, the mixture was cooled to 0° C. and water (20 mL) was slowly added. The pH was adjusted to 1 with 3M aqueous hydrochloric acid and then the mixture was stirred for 30 minutes. The aqueous layer was extracted with diethyl ether and ethyl acetate and then made basic with sodium hydroxide pellets which resulted in the separation of an oil. The mixture was extracted with ethyl acetate and the organic layer was dried and evaporated under reduced pressure. The residue was triturated with diethyl ether to give the title compound (0.54 g, 25%) as a yellow solid.

Workup

  1. extractionThe aqueous layer was extracted with diethyl ether and ethyl acetate
  2. customresulted in the separation of an oil
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe organic layer was dried
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-2fed42b54a77460c8506a0f025d21af6
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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