Dimethylamine → (1H-Perimidin-2-yl)methyl dimethylcarbamate

HRID 1287827Notes

Reaction equation

HRID 1287827 reaction equation
[CH:1]1[C:12]2=[C:13]3[C:4](=[CH:5][CH:6]=[CH:7][C:8]3=[N:9][C:10]3[N:11]2[CH2:14][O:15][CH:16]=3)[CH2:3][CH:2]=1.[CH3:17][NH:18][CH3:19].C(COC)[O:21]C>>[CH3:17][N:18]([CH3:19])[C:14](=[O:21])[O:15][CH2:16][C:10]1[NH:9][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:13]=2[C:12]([N:11]=1)=[CH:1][CH:2]=[CH:3]3

Participants

4

Reactant 3

HCID 674DimethylamineHCID 80711,2-DimethoxyethaneHCID 21506591HCID 21506591, compound

Product 1

HCID 21506587(1H-Perimidin-2-yl)methyl dimethylcarbamate

Procedure

A 10 g (0.44 mole) sample of 1H, 3H-oxazolo[3,4-a]perimidine, 3-one is dissolved in glyme at 30°, and the resulting solution is treated with excess 40% aqueous dimethylamine for 10 min. The mixture is then concentrated, dissolved in CHCl3, washed with water and dried. Further concentration gives an oil which is crystallized from ethyl acetate-cylcohexane and is then recrystallized from the same solvents twice to give the desired product, (2-perimidyl)methyl N,N-dimethylcarbamate, as yellow crystals, m.p. 161°-162° C.

Workup

  1. concentrationThe mixture is then concentrated
  2. dissolutiondissolved in CHCl3
  3. washwashed with water
  4. customdried
  5. concentrationFurther concentration
  6. customgives an oil which
  7. customis crystallized from ethyl acetate-cylcohexane
  8. customis then recrystallized from the same solvents twice

Sources & evidence

ORD record
ord-d2fa8fc6d82941f58777fab28da6f613
Source dataset
uspto-grants-1976_10
Patent number
US03985880

Reaction notes

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