4-Toluenesulfonyl chloride → 5-(N'-cyano-N"-methylguanidino)pentyl p-toluenesulphonate

HRID 1733122Notes

Reaction equation

HRID 1733122 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.[C:12]([NH:14][C:15]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[N:16][CH3:17])#[N:13]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:15]([NH:16][CH3:17])=[N:14][C:12]#[N:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 54552768N-cyano-N'-(5-hydroxypentyl)-N"-methylguanidine

Product 1

HCID 1784850465-(N'-cyano-N"-methylguanidino)pentyl p-toluenesulphonateYield 42.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of p-toluenesulphonyl chloride (9.11 g) in pyridine (40 ml) was added in portions to a stirred solution of N-cyano-N'-(5-hydroxypentyl)-N"-methylguanidine (8.0 g) in pyridine (40 ml) at -10°. The mixture was stirred at 2° for 40 hours and was poured into ice-water. The aqueous mixture was extracted with chloroform, and the extracts were washed with dilute hydrochloric acid and evaporated to give 5-(N'-cyano-N"-methylguanidino)pentyl p-toluenesulphonate (6.3 g) as an orange oil.

Workup

  1. extractionThe aqueous mixture was extracted with chloroform
  2. washthe extracts were washed with dilute hydrochloric acid
  3. customevaporated

Sources & evidence

ORD record
ord-042c7e359b824ba7843cdad2c76516bc
Source dataset
uspto-grants-1980_12
Patent number
USRE030457

Reaction notes

Loading…