Triethylamine → HCID 57962249, compound

HRID 541831Notes

Reaction equation

HRID 541831 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[N+:27]([C:30]1[CH:31]=[C:32]([CH2:36][C:37](O)=[O:38])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]>C(Cl)Cl.O1CCCC1>[N+:27]([C:30]1[CH:31]=[C:32]([CH2:36][C:37]([NH:1][C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=2)=[O:38])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 24386Thionyl ChlorideHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Product 1

HCID 57962249HCID 57962249, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl (3-aminophenyl)carbamate (1.0 g, 4.8 mmol) was dissolved in methylene chloride (4 mL) and then thionyl chloride (2.0 mL, 27 mmol) was added. The mixture was heated at 80° C. for 1 h. The solvent was removed under vacuum. Tetrahydrofuran (20 mL), triethylamine (2.3 mL, 17 mmol) and (3-nitrophenyl)acetic acid (0.87 g, 4.8 mmol) were then added and the mixture was stirred at rt for 1 h. The solvent was removed under vacuum and then EtOAc and water were added. The aqueous phase was extracted again with EtOAc. The organics were combined, dried over Na2SO4 and concentrated to give the desired product as a white powder (1.70 g, 95%). LCMS for C19H21N3O5 (M-tBu+H)+: m/z=316.0.

Workup

  1. customThe solvent was removed under vacuum
  2. customThe solvent was removed under vacuum
  3. additionEtOAc and water were added
  4. extractionThe aqueous phase was extracted again with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e2541d32f1104380a9192b61b1a40acb
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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