Chlorosulfonic acid → HCID 20572145, compound

HRID 1577300Notes

Reaction equation

HRID 1577300 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([CH3:9])[CH:5]=[C:4]([NH:10][CH:11]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[N:3]=1.Cl[S:20]([OH:23])(=[O:22])=[O:21].C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[OH-:8].[NH2:1][C:2]1[N:3]=[C:4]([NH:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH:5]=[C:6]([CH3:9])[N+:7]=1[O:8][S:20]([OH:23])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 81531DiisopropylethylamineHCID 178428203HCID 178428203, compound

Product 1

HCID 20572145HCID 20572145, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.00 grams of 2-amino-4-methyl-6-(cyclooctylamino)pyrimidine-3-oxide, 1.00 grams of chlorosulfonic acid, and 2.5 g of di-isopropylethylamine 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-(cyclooctylamino)-1-(sulfooxy)pyrimidinium 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-2ea4d1b1b6bc47aab2a2010e807d37cc
Source dataset
uspto-grants-1981_09
Patent number
US04287338

Reaction notes

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