N-Iodosuccinimide → HCID 178433376, compound

HRID 1580428Notes

Reaction equation

HRID 1580428 reaction equation
[CH3:1][C:2]1[NH:8][C:7]([NH2:9])=[N:6][C:4](=[O:5])[CH:3]=1.[I:10]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:9][C:7]1[N:6]=[C:4]([OH:5])[C:3]([I:10])=[C:2]([CH3:1])[N:8]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178429414HCID 178429414, compound

Product 1

HCID 178433376HCID 178433376, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

With protection from external moisture throughout, 250.3 mg. (2.0 millimoles) of finely powdered 6-methyl-isocytosine is dissolved in 4 ml. of hot glacial acetic acid. While still hot, 450 mg. (2.0 millimoles) of N-iodosuccinimide is added to the solution and the whole is heated on a steam bath for five minutes with occasional swirling. The reaction mixture is removed from the steam bath and allowed to stand at ambient temperature. After three and one-half hours, water is added, the crystalline cake is crushed, the solid collected, washed with water, then acetone and dried in air. The crude material [335 mg.] is crystallized from approximately 10 ml. of glacial acetic acid. After being kept at room temperature overnight, the pure compound is collected, washed with its mother liquor, then with anhydrous ether repeatedly and dried in vacuo at ca. 90°C. There is thus obtained 220 mg. of 2-amino-5-iodo-6-methyl-4-pyrimidinol which melts at 211.5° to 212.5°C. with previous darkening and sintering, has λ max0.1N NaOH 236 nm. (ε9,900); 284 nm. (ε10,900) and the infrared absorption below.

Workup

  1. temperaturethe whole is heated on a steam bath for five minutes
  2. customThe reaction mixture is removed from the steam bath
  3. customto stand at ambient temperature
  4. additionAfter three and one-half hours, water is added
  5. customthe crystalline cake is crushed
  6. customthe solid collected
  7. washwashed with water
  8. dry with materialacetone and dried in air
  9. customThe crude material [335 mg.] is crystallized from approximately 10 ml
  10. customthe pure compound is collected
  11. washwashed with its mother liquor
  12. dry with materialwith anhydrous ether repeatedly and dried in vacuo at ca. 90°C
  13. custom(ε10,900) and the infrared absorption below

Sources & evidence

ORD record
ord-8338b8ce4faa4d25b10c655770f3a6d6
Source dataset
uspto-grants-1976_01
Patent number
US03932617

Reaction notes

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