m-Chloroperbenzoic acid → HCID 178477626, compound

HRID 1577829Notes

Reaction equation

HRID 1577829 reaction equation
[NH2:1][C:2]1[C:3]([OH:14])=[N:4][C:5]([NH:8][CH2:9][CH2:10][S:11][CH2:12][CH3:13])=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>CO.C(Cl)Cl>[NH2:1][C:2]1[C:3]([OH:14])=[N:4][C:5]([NH:8][CH2:9][CH2:10][S:11]([CH2:12][CH3:13])=[O:23])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178477442HCID 178477442, compound

Product 1

HCID 178477626HCID 178477626, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3.2 gm of 5-amino-2-(2'-ethylmercapto-ethylamino)4-hydroxy-pyrimidine (0.015 mol) were dissolved in a mixture of 60 ml of absolute methanol and 60 ml of absolute methylene chloride. The solution was admixed with a solution of 2.89 gm (0.015 mol) of m-chloro-perbenzoic acid in 50 ml of methylene chloride at -15° C. After stirring for 8 hours at 0° C., the mixture was evaporated in vacuo to nearly dryness and was fractionated on a silicagel column with a methylene chloride/methanol mixture of at first 10:1, then 5:1. 1.42 gm (41.1%) of a uniform product were obtained.

Workup

  1. customthe mixture was evaporated in vacuo to nearly dryness
  2. additionwas fractionated on a silicagel column with a methylene chloride/methanol mixture of at first 10:1

Sources & evidence

ORD record
ord-5597ee67620149298961bda52557f4e5
Source dataset
uspto-grants-1981_09
Patent number
US04289775

Reaction notes

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