Chloroform → HCID 86676000, compound

HRID 1855108Notes

Reaction equation

HRID 1855108 reaction equation
C(Cl)(Cl)Cl.[C:5]([O:9][C:10]([C:12]1[C:17]([NH2:18])=[CH:16][CH:15]=[C:14]([CH3:19])[N+:13]=1[O-:20])=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(C(C)C)CC)(C)C.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O>[C:5]([O:9][C:10]([C:12]1([C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:17]([NH2:18])=[CH:16][CH:15]=[C:14]([CH3:19])[NH+:13]1[O-:20])=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 71224964HCID 71224964, compound

Product 1

HCID 86676000HCID 86676000, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

4 mL of a chloroform solution containing 0.45 g (2 mmol) of 2-t-butoxycarbonyl amino-6-methyl pyridine-N-oxide and 0.26 g (2 mmol) of diisopropylethylamine was prepared, and was adjusted to 10° C. 0.29 g (2 mmol) of benzoyl chloride was added dropwise to the solution over 10 minutes at 10° C. After stirring further for 40 minutes at 10° C., 5 mL of water was added thereto, followed by liquid separation. The chloroform layer obtained by liquid separation was washed twice with 5 mL of water, and then dried with magnesium sulfate, followed by filtration. The resulting solution was concentrated under reduced pressure and dried to obtain 0.64 g of 2-t-butoxycarbonyl-2-benzoyl amino-6-methyl pyridine-N-oxide (yield: 97%) in the form of yellow-brown amorphous which was the target product.

Workup

  1. customwas prepared
  2. customwas adjusted to 10° C
  3. customfollowed by liquid separation
  4. customThe chloroform layer obtained by liquid separation
  5. washwas washed twice with 5 mL of water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfollowed by filtration
  8. concentrationThe resulting solution was concentrated under reduced pressure
  9. customdried

Sources & evidence

ORD record
ord-e9f33a1654514a068c85b21faf4d7abf
Source dataset
uspto-grants-2015_02
Patent number
US08962849B2

Reaction notes

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