Ammonium Chloride → HCID 9883507, compound

HRID 1385215Notes

Reaction equation

HRID 1385215 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2([C:19]#[N:20])[CH:16]3[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)[CH:6]=[CH:7][CH:8]=1)[CH3:2].[NH4+:21].[Cl-:22].C[Al](C)C>C1(C)C=CC=CC=1>[ClH:22].[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2([C:19](=[NH:21])[NH2:20])[CH:10]3[CH2:18][CH:14]4[CH2:13][CH:12]([CH2:17][CH:16]2[CH2:15]4)[CH2:11]3)[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 18624266HCID 18624266, compound

Product 1

HCID 9883507HCID 9883507, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-(3-ethylphenyl)-2-adamantanecarbonitrile (265 mg, 1 mmol) and NH4Cl (107 mg, 2 mmol) in dry toluene (5 mL) under argon was treated dropwise with 2-M trimethylaluminium in toluene (1.0 mL, 2 mmol), refluxed for 12 h, cooled to room temperature and purified directly by chromatography [SiO2; EtOAc—MeOH (9:1)] to give the title compound (178 mg, 56%) as a white solid: mp >300° C.; IR νmax (Nujol)/cm−1 2921, 2855, 1669, 1454, 1377, 1089, 798, 744 and 704; NMR δH (400 MHz, DMSO-d6) 1.18 (3H, t, J 8.0 Hz), 1.55-1.69 (7H, m), 1.83 (5H, s), 2.60 (2H, q, J 8.0 Hz), 3.15 (2H, s), 7.10-7.17 (1H, m), 7.27-7.38 (3H, m) and 8.88 (4H, br s); Anal. Calcd for C19H27ClN2.0.35 H2O: C, 70.18; H, 8.59; N, 8.61. Found: C, 70.25; H, 8.41; N, 8.46.

Workup

  1. temperaturerefluxed for 12 h
  2. custompurified directly by chromatography [SiO2; EtOAc—MeOH (9:1)]

Sources & evidence

ORD record
ord-dfc875f54c674aab935c12aa7164e60f
Source dataset
uspto-grants-2001_07
Patent number
US06262106B1

Reaction notes

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