Triethylamine → HCID 86675999, compound

HRID 1855106Notes

Reaction equation

HRID 1855106 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([CH3:15])[N+:9]=1[O-])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)([O-:19])=[O:18].C(N(CC)CC)C.[Cl:36]C(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([C:8]1([C:24](=[O:25])[C:23]2[CH:22]=[CH:21][C:20]([N+:17]([O-:19])=[O:18])=[CH:28][CH:27]=2)[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([CH2:15][Cl:36])[NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 85024-Nitrobenzoyl chlorideHCID 94429TriphosgeneHCID 71224964HCID 71224964, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 86675999HCID 86675999, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Conditions

Temperature
-15 °C

Procedure

1 ml of a chloroform solution containing 0.22 g (1.0 mmol) of 2-t-butoxycarbonyl amino-6-methyl pyridine-N-oxide was added dropwise to 5 mL of a chloroform solution containing 2.0 mmol of para-nitrobenzoyl chloride over 10 minutes at room temperature. After 20 minutes had elapsed therefrom, the reaction mixture was cooled to −15° C., and 0.30 g (3.0 mmol) of triethylamine was added dropwise thereto over 5 minutes. After 5 minutes had elapsed therefrom, 1 ml of a chloroform solution containing 0.20 g (0.67 mmol) of triphosgene was added dropwise thereto over a period of 5 minutes. After 20 minutes had elapsed therefrom, 0.20 g (2.0 mmol) of triethylamine was added dropwise thereto over 5 minutes, and the resulting mixture was then stirred for 30 minutes. The resulting reaction solution was poured into saturated sodium bicarbonate water, and was extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated. The resulting crude product was purified by column chromatography (hexane/ethyl acetate) to obtain 2-t-butoxycarbonyl-2-para-nitrobenzoyl amino-6-chloromethyl pyridine which was the target product with a yield of 64% (as measured by HPLC).

Workup

  1. waitover 5 minutes
  2. waitAfter 5 minutes had elapsed
  3. additionwas added dropwise
  4. waitover a period of 5 minutes
  5. waitAfter 20 minutes had elapsed
  6. waitover 5 minutes
  7. customThe resulting reaction solution
  8. extractionwas extracted with ethyl acetate
  9. dry with materialThe organic layer was dried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe resulting crude product was purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9f1d88eefe834a27a3cd2ec1b5af69a5
Source dataset
uspto-grants-2015_02
Patent number
US08962849B2

Reaction notes

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