Hydrochloric Acid → HCID 86715962, compound

HRID 2283210Notes

Reaction equation

HRID 2283210 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:16])[CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH:5]=[CH:6][CH:7]=1.Cl.[N-:18]=[N+:19]=[N-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O>[N:1]([C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:16])[CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH:5]=[CH:6][CH:7]=1)=[N+:18]=[N-:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 16779355856047-84-2

Product 1

HCID 86715962HCID 86715962, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

N-(3-Aminophenyl)-2-(diethylamino)acetamide 5 (0.52 g, 2.35 mmol) was dissolved in THF (6 ml), and cooled in an ice bath. The resulting stirred mixture was treated sequentially with concentrated aqueous HCl (1.08 ml, 12.92 mmol), then with tBuONO (0.61 g, 5.87 mmol). The reaction was stirred in an ice bath for 1.5 hours and after that time NaN3 (0.46 g, 7.05 mmol) was added, followed by careful addition of water, until the reaction ceased to effervesse. The reaction was allowed to warm to room temperature and stirred overnight. The mixture was carefully neutralised with saturated aqueous NaHCO3 solution and THF was evaporated in vacuo. The aqueous solution was extracted three times with EtOAc (75 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo, to give N-(3-azidophenyl)-2-(diethylamino)acetamide 6 as a dark brown oil (0.56 g, 85%) without requiring any further purification; Rf 0.24 [10% MeOH in DCM]; IR (film): 3279.67, 2934.63, 2110.57, 1687.86, 1515.73 cm−1; δH (CDCl3, 400 MHz) 9.43 (1H, s, NH), 7.41 (1H, m, ArH), 7.30-7.23 (2H, m, 2×ArH), 6.76 (1H, td, J1=8.0, J2=2.0 Hz, ArH), 3.13 (2H, s, CH2), 2.64 (4H, m, 2×CH2), 1.08 (6H, m, 2×CH3); δC (CDCl3, 100 MHz) 170.25 (C═O), 140.95 (Ar—C), 139.18 (Ar—C), 130.14 (Ar—CH), 115.60 (Ar—CH), 114.48 (Ar—CH), 109.96 (Ar—CH), 58.11 (CH2), 48.92 (2×CH2), 12.40 (2×CH3); LC-MS (5 min) m/z 248.49 [C12H17N5O+H]+ (25), 220.07 [(C12H17N5O+H)-28]+ (40) Rt 2.05 min; HRMS m/z calc. C12H18N5O [M+H]+248.1506. found [M+H]+ 247.1498.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe reaction was stirred in an ice bath for 1.5 hours
  3. stirringstirred overnight
  4. customwas evaporated in vacuo
  5. extractionThe aqueous solution was extracted three times with EtOAc (75 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-50c62c9cadbb499295097a5b1a08454f
Source dataset
uspto-grants-2015_09
Patent number
US09145377B2

Reaction notes

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