O-Xylene → HCID 21510116, compound

HRID 1576854Notes

Reaction equation

HRID 1576854 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N([C:16]1[NH:17][CH2:18][CH2:19][CH2:20][N:21]=1)[N+]([O-])=O.C1(C)C(C)=CC=CC=1>O>[NH:21]1[CH2:20][CH2:19][CH2:18][N:17]=[C:16]1[NH:1][CH2:2][CH2:3][CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 1215483-Amino-1-phenylpropan-1-olHCID 412214N-(1,4,5,6-Tetrahydropyrimidin-2-yl)nitramide

Product 1

HCID 21510116HCID 21510116, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8 parts of α-(2-aminoethyl)benzylalcohol, 7.2 parts of 2-(nitramino)-1,4,5,6-tetrahydropyrimidine and 40 parts of xylene is stirred and refluxed for 48 hours with water-separator. Upon cooling the reaction mixture, the product is separated as an oil. The xylene is decanted and the oily product is triturated in diisopropylether. The solid product is filtered off and crystallized from acetone, yielding α-[2-(1,4,5,6-tetrahydro-2-pyrimidinylamino)ethyl]benzylalcohol; m.p. 130°-135°C.

Workup

  1. temperatureUpon cooling the reaction mixture
  2. customthe product is separated as an oil
  3. customThe xylene is decanted
  4. customthe oily product is triturated in diisopropylether
  5. filtrationThe solid product is filtered off
  6. customcrystallized from acetone

Sources & evidence

ORD record
ord-4867107140ef49bdbfe7188386f1b173
Source dataset
uspto-grants-1976_09
Patent number
US03983133

Reaction notes

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