3-Methoxypropylamine → HCID 70358994, compound

HRID 1164914Notes

Reaction equation

HRID 1164914 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:8]1([S:14](Cl)(=[O:16])=[O:15])[NH:12][C:11]([Cl:13])=[CH:10][S:9]1>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]([NH:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[S:14]([C:8]1[S:9][CH:10]=[C:11]([Cl:13])[N:12]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 16723-MethoxypropylamineHCID 22164315HCID 22164315, compound

Product 1

HCID 70358994HCID 70358994, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

40 g of 3-methoxy-n-propylamine were added dropwise at room temperature to a solution of 25.25 g (0.1 mol) of 2,4-dichlorothiazole-sulphonyl chloride from Example 1 in 600 ml of THF, and the mixture was subsequently stirred for 30 minutes at room temperature. After concentrating under a waterpump vacuum, the mixture was stirred with 400 ml of water, the aqueous phase was extracted twice using methylene chloride, and the combined organic phases were dried over magnesium sulphate. After removing the solvent under a waterpump vacuum, 31.3 g of a brown oil were obtained which was chromatographed on silica gel using toluene/ethanol (5:1) as the eluent. 29.3 g (79%) of product were obtained, m.p.: 55° C.

Workup

  1. concentrationAfter concentrating under a waterpump vacuum
  2. stirringthe mixture was stirred with 400 ml of water
  3. extractionthe aqueous phase was extracted twice using methylene chloride
  4. dry with materialthe combined organic phases were dried over magnesium sulphate
  5. customAfter removing the solvent under a waterpump vacuum

Sources & evidence

ORD record
ord-08526cb493db4c4fa72f8e465c191325
Source dataset
uspto-grants-1990_03
Patent number
US04906650

Reaction notes

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