Sodium Carbonate → HCID 86674684, compound

HRID 571821Notes

Reaction equation

HRID 571821 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[Cl:21].ClC(Cl)(O[C:26](=[O:32])OC(Cl)(Cl)Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+].[NH2:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[C:44]#[N:45]>ClCCl.O>[Cl:21][C:3]1[CH:4]=[C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:9]2)[CH:6]=[CH:7][C:2]=1[NH:1][C:26]([NH:40][C:41]1[CH:48]=[CH:47][CH:46]=[C:43]([C:44]#[N:45])[CH:42]=1)=[O:32]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 167023-AminobenzonitrileHCID 94429TriphosgeneHCID 68325445HCID 68325445, compound

Product 1

HCID 86674684HCID 86674684, compoundYield 296.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl (RS)-2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate (70 mg) in dichloromethane (2 ml) was added triphosgene (25 mg). A solution of sodium carbonate (47 mg) in water (2 ml) was then added. The reaction mixture was stirred at room temperature for 2.5 hours. TLC showed all the starting material had reacted. 3-Aminobenzonitrile (53 mg, CAS 2237-30-1) was then added and the reaction mixture was stirred at room temperature for a further 2 hours. TLC showed the reaction was complete. The reaction mixture was poured into dichloromethane and extracted with water. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: 0% to 30% EtOAc in hexanes) to give tert-butyl (RS)-2-(3-chloro-4-(3-(3-cyanophenyl)ureido)phenyl)morpholine-4-carboxylate (114 mg, quant.) as an amorphous white solid. MS (ISP): 457.2 ([{37Cl}M−H]−), 455.2 ([{35Cl}M−H]−).

Workup

  1. customhad reacted
  2. stirringthe reaction mixture was stirred at room temperature for a further 2 hours
  3. extractionextracted with water
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2; gradient: 0% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6456bee792594db9b7e32b415450dcd7
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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