Ammonia → HCID 67304797, compound

HRID 1009030Notes

Reaction equation

HRID 1009030 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([S:11](Cl)(=[O:13])=[O:12])[S:8][C:9]=1[CH3:10].[NH3:15]>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([S:11]([NH2:15])(=[O:13])=[O:12])[S:8][C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86630948HCID 86630948, compound

Product 1

HCID 67304797HCID 67304797, compoundYield 118%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the above prepared 4-(2-methoxy-ethyl)-5-methyl-thiophene-2-sulfonyl chloride (4.59 g, 18 mmol) in DCM (18 mL) were added 25% aqueous NH3 (9 mL, ˜120 mmol) and the biphasic reaction mixture was vigorously stirred at rt for 3 h. After the addition of DCM (120 mL) the reaction mixture was washed with H2O (2×120 mL) and the aqueous layers were extracted with DCM (50 mL). The combined organic layers were dried (Na2SO4) and evaporated affording 5.0 g crude product as a yellow viscous oil which was purified by chromatography over silica with hexane-ethyl acetate 2:1 providing 3.62 g (85% GC 96.3%) yellow viscous oil. ESI-MS (m/z) 253 (M+NH4+, 100).

Workup

  1. customthe biphasic reaction mixture
  2. washwas washed with H2O (2×120 mL)
  3. extractionthe aqueous layers were extracted with DCM (50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-9b818de1bb7142e8ac3988db6aed6e5c
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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