Ammonia → HCID 67273589, compound

HRID 1696762Notes

Reaction equation

HRID 1696762 reaction equation
Cl[S:2]([C:5]1[S:9][C:8]([CH2:10][CH2:11][O:12][C:13](=[O:15])[CH3:14])=[C:7]([CH3:16])[CH:6]=1)(=[O:4])=[O:3].[NH3:17]>C(Cl)Cl>[CH3:16][C:7]1[CH:6]=[C:5]([S:2](=[O:4])(=[O:3])[NH2:17])[S:9][C:8]=1[CH2:10][CH2:11][O:12][C:13](=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 87333231Acetic acid 2-(5-chlorosulfonyl-3-methyl-thiophen-2-yl)-ethyl ester

Product 1

HCID 67273589HCID 67273589, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the above prepared crude acetic acid 2-(5-chlorosulfonyl-3-methyl-thiophen-2-yl)-ethyl ester (53.3 g, ca. 177 mmol) in DCM (180 mL) were added 25% aqueous NH3 (53 mL, ˜700 mmol) and the biphasic reaction mixture was vigorously stirred at rt for 18 h. After the addition of DCM (1200 mL) the reaction mixture was washed with 10% brine (2×400 mL) and the aqueous layers were extracted with DCM (600 mL). The combined organic layers were dried (Na2SO4) and evaporated affording 48.5 g yellow crystalline residue which was crystallized from hot isobutyl acetate (500 mL) affording 34.8 g (74.7%, GC 97.9%) product as a off white powder. ESI-MS (m/z) 286 (M+Na+, 59); 264 (M+H+, 19).

Workup

  1. customthe biphasic reaction mixture
  2. washwas washed with 10% brine (2×400 mL)
  3. extractionthe aqueous layers were extracted with DCM (600 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7882984e277746f3b787c92fbdb8ccab
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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