Water → HCID 18978368, compound

HRID 2392991Notes

Reaction equation

HRID 2392991 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][NH:13][CH2:14][CH2:15][CH2:16][NH2:17].[OH2:18]>CN(C)C=O>[CH3:12][N:13]([CH2:14][CH2:15][CH2:16][NH:17][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:8])=[O:18])[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 80511N-Methyl-1,3-propanediamine

Product 1

HCID 18978368HCID 18978368, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

--A freshly prepared solution of p-toluenesulfonyl chloride (90.8 g, 0.476 mole) in N,N-dimethylformamide (200 ml) is added during 45 min. with moderate external cooling to a stirred solution of N-methyl-1,3-propanediamine (41.9 g, 0.476 mole) in N,N-dimethylformamide (150 ml) at such a rate that the temperature does not exceed 40° C. The mixture is stirred 45 min. longer at room temperature and then poured into cold water (1.2 1.). The white gum that precipitated, solidifies on standing. The crude product is collected, pulverized, and washed thoroughly with water. Recrystallization from ethanol affords the pure product, m.p. 93° C. (Kofler Heizbank), in 79% yield (74.4 g).

Workup

  1. customdoes not exceed 40° C
  2. customThe white gum that precipitated
  3. customThe crude product is collected
  4. washwashed thoroughly with water
  5. customRecrystallization from ethanol
  6. customaffords the pure product, m.p. 93° C. (Kofler Heizbank)

Sources & evidence

ORD record
ord-9f5c9354b0484e4483145b606607c02f
Source dataset
uspto-grants-1998_09
Patent number
US05804571

Reaction notes

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