Methanesulfonyl chloride → HCID 4417387, compound

HRID 704622Notes

Reaction equation

HRID 704622 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH3:11])=[O:9])=[C:5]([CH3:7])[N:6]=1.[S:12](Cl)([CH3:15])(=[O:14])=[O:13]>N1C=CC=CC=1>[S:12]([NH:1][C:2]1[S:3][C:4]([C:8]([O:10][CH3:11])=[O:9])=[C:5]([CH3:7])[N:6]=1)([CH3:15])(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 713653methyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 4417387HCID 4417387, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of methyl 2-amino-4-methylthiazole-5-carboxylate (3.72 g) and pyridine (25 ml) was added mesyl chloride (1.6 ml) over the period of 5 minutes under cooling with stirring, and the mixture was stirred for 1 hour at ambient temperature and for 3 hours for 40° C. After the reaction mixture was concentrated, ethyl acetate (50 ml) and tetrahydrofuran (20 ml) were added to the residue and the mixture was adjusted to pH 3 with diluted hydrochloric acid. The separated organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was pulverised with diethyl ether to give methyl 2-mesylamino-4-methylthiazole-5-carboxylate (3.5 g).

Workup

  1. temperatureunder cooling
  2. stirringthe mixture was stirred for 1 hour at ambient temperature and for 3 hours for 40° C
  3. concentrationAfter the reaction mixture was concentrated
  4. additionethyl acetate (50 ml) and tetrahydrofuran (20 ml) were added to the residue
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c7437404466648b5a3d022bae876b963
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

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