Water → HCID 66605621, compound

HRID 2359729Notes

Reaction equation

HRID 2359729 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].CCN(CC)CC.[I:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][S:26](Cl)(=[O:28])=[O:27].O>O1CCOCC1>[I:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][S:26]([NH:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15832487Methyl 4-amino-1,3-thiazole-5-carboxylateHCID 184673992-Iodobenzenemethanesulfonyl chloride

Product 1

HCID 66605621HCID 66605621, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2 g (12.64 mmol) of methyl 4-amino-1,3-thiazole-5-carboxylate were dissolved together with 5.1 ml (63.2 mmol) NEt3 in 20 ml of dioxane, and 4.4 g (13.9 mmol) of (2-iodophenyl)methanesulfonyl chloride were added at room temperature. The reaction mixture was stirred at RT for 5 h. Then 40 ml of water were added and the mixture was extracted repeatedly with ethyl acetate. The combined organic phases were washed with 2N HCl, dried and concentrated. The residue was purified by means of column chromatography (SiO2, gradient ethyl acetate/n-heptane 10:90 to 75:25). This gave 4.3 g of methyl 4-{[(2-iodobenzyl)sulfonyl]amino}-1,3-thiazole-5-carboxylate.

Workup

  1. additionwere added at room temperature
  2. extractionthe mixture was extracted repeatedly with ethyl acetate
  3. washThe combined organic phases were washed with 2N HCl
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by means of column chromatography (SiO2, gradient ethyl acetate/n-heptane 10:90 to 75:25)

Sources & evidence

ORD record
ord-91678759bb934f4a98d0153a147d1216
Source dataset
uspto-grants-2014_04
Patent number
US08686000B2

Reaction notes

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