Triethylamine → HCID 178525191, compound

HRID 1752026Notes

Reaction equation

HRID 1752026 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:3].[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1.CCN(CC)CC>C(Cl)Cl>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][O:4][C:2]([C:23]2[C:18]3[N:17]=[N:16][NH:15][C:19]=3[CH:20]=[CH:21][CH:22]=2)=[O:3])=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 782054-Nitrobenzyl chloroformateHCID 178418385HCID 178418385, compound

Product 1

HCID 178525191HCID 178525191, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

p-Nitrobenzyl chloroformate (0.5 mmol) was dissolved in 5 mL of CH2Cl2 and treated with benzotriazole (0.5 mmol) using Et3N (2 mmol) as base. The mixture was stirred overnight at room temperature, diluted with CH2Cl2 (20 mL) and washed with 3×5 mL of 1N HCl, 2×5 mL of 1N NaOH and 1×5 mL of brine. The organic phase was dried and filtered. The volatiles were removed and the product was triturated with diethyl ether to provide a pale yellow solid (59% yield). mp 160-162° C. 1H NMR (CDCl3) δ 8.27 (d, 1H, J=8.9 Hz), 8.17 (m, 3H), 7.72 (d, 1H, J=8.9 Hz), 7.65 (td, 1H, J=8.3 Hz, 1.1 Hz), 7.53 (m, 2H), 5.26 (s, 2H). 13C NMR (CDCl3) δ 154.84, 146.17, 142.27, 141.30, 132.01, 130.82, 128.78, 126.37, 124.16, 120.86, 113.58, 68.66. HRMS (FAB) calcd for C14H11N4O4 ([M+H]+): 299.0775. found 297.0775.

Workup

  1. washwashed with 3×5 mL of 1N HCl, 2×5 mL of 1N NaOH and 1×5 mL of brine
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customThe volatiles were removed
  5. customthe product was triturated with diethyl ether

Sources & evidence

ORD record
ord-a47311d3a9b24456814c0c3b453a7d83
Source dataset
uspto-grants-2015_10
Patent number
US09162991B2

Reaction notes

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