Methylamine → HCID 22164323, compound

HRID 1164907Notes

Reaction equation

HRID 1164907 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1([S:10](Cl)(=[O:12])=[O:11])[NH:8][C:7]([Cl:9])=[CH:6][S:5]1>C1COCC1>[CH3:1][NH:2][S:10]([C:4]1([Cl:3])[NH:8][C:7]([Cl:9])=[CH:6][S:5]1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22164315HCID 22164315, compound

Product 1

HCID 22164323HCID 22164323, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

21 g of a 30% strength aqueous methylamine solution were added dropwise at approx. -75° C. in the course of 45 minutes to 25.25 g (0.1 mol) of 2,4-dichloro-thiazole-sulphonyl chloride from Example 1 in 250 ml of THF, the cold bath was then removed and the temperature was subsequently allowed to rise to room temperature, the mixture was subsequently stirred for 30 minutes, the resulting suspension was evaporated under a waterpump vacuum, and the residue was stirred with 300 ml of water. The solid was filtered off with suction and chromatographed on silica gel (eluent toluene/EtOH 15:1) in order to remove small amounts of starting material and product which is substituted in the 2-position.

Workup

  1. customthe cold bath was then removed
  2. customto rise to room temperature
  3. customthe resulting suspension was evaporated under a waterpump vacuum
  4. stirringthe residue was stirred with 300 ml of water
  5. filtrationThe solid was filtered off with suction
  6. customchromatographed on silica gel (eluent toluene/EtOH 15:1) in order
  7. customto remove small amounts of starting material and product which

Sources & evidence

ORD record
ord-c67f0e67f5d245c890e239053aeb9fcc
Source dataset
uspto-grants-1990_03
Patent number
US04906650

Reaction notes

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