Diisopropylamine → HCID 70568794, compound

HRID 1577298Notes

Reaction equation

HRID 1577298 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:16])[N+:3]=1[O-:17].Cl[S:19]([OH:22])(=[O:21])=[O:20].C(NC(C)C)(C)C>C(Cl)(Cl)Cl>[OH-:17].[NH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH2:14][CH2:15]2)[CH:5]=[C:4]([CH3:16])[N+:3]=1[O:17][S:19]([OH:22])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 24638Chlorosulfonic acidHCID 178428004HCID 178428004, compound

Product 1

HCID 70568794HCID 70568794, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.00 grams of 2-amino-6-methyl-4-(3,4,7,8-tetrahydro-1-(2H)-azocinyl)-pyridine-1-oxide, 1.00 grams of chlorosulfonic acid, and 2.5 grams of diisopropylamine in 25 ml of chloroform is stirred overnight. The mixture is concentrated in vacuo. The residue is stirred with aqueous sodium bicarbonate, filtered and washed with ether to give the crude product. This is recrystallized from DMF and ethyl acetate to yield the purified 2-amino-6-methyl-4-(3,4,7,8-tetrahydro-1(2H)-azocinyl)-1-(sulfooxy)-pyridinium hydroxide, inner salt.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. stirringThe residue is stirred with aqueous sodium bicarbonate
  3. filtrationfiltered
  4. washwashed with ether
  5. customto give the crude product
  6. customThis is recrystallized from DMF and ethyl acetate

Sources & evidence

ORD record
ord-71bf7e3c1afc463093f72f277c17aba7
Source dataset
uspto-grants-1981_09
Patent number
US04287338

Reaction notes

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