Chloromethyl Methyl Ether → HCID 68679074, compound

HRID 1172401Notes

Reaction equation

HRID 1172401 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1.C(N(CC)C(C)C)(C)C.Cl[CH2:27][O:28][CH3:29]>C(Cl)(Cl)Cl>[CH3:27][O:28][CH2:29][N:3]1[CH:4]=[CH:5][S:1][C:2]1=[N:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 57562673HCID 57562673, compound

Product 1

HCID 68679074HCID 68679074, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 4.85 g (20.6 mmol) of methyl 6-(thiazol-2-ylamino)-pyridine-2-carboxylate, 7.20 ml (41.2 mmol) of N,N-diisopropylethylamine and 100 ml of chloroform was added 2.35 ml (30.9 mmol) of chloromethylmethyl ether followed by stirring at room temperature for 1 hour. The reaction mixture was washed with 100 ml of water for three times and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to about 20 ml in total and the resulting solid was filtered. The resulting solid was washed with ether and dried in vacuo to give 6.38 g (20.6 mmol) of the title compound as a white solid.

Workup

  1. washThe reaction mixture was washed with 100 ml of water for three times
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to about 20 ml in total
  5. filtrationthe resulting solid was filtered
  6. washThe resulting solid was washed with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-eab0ee35d0c6426dbfca6e876d7a2f47
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

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