Acetic Anhydride → 3-(3-trifluoromethylphenyl)-6-[(N-acetyl)-n-butylamino]-tetrahydro-1,3,5-triazine-2,4-dione

HRID 126758Notes

Reaction equation

HRID 126758 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([N:9]2[C:14](=[O:15])[NH:13][CH:12]([NH:16][CH2:17][CH2:18][CH2:19][CH3:20])[NH:11][C:10]2=[O:21])[CH:6]=[CH:7][CH:8]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[F:23][C:2]([F:22])([F:1])[C:3]1[CH:4]=[C:5]([N:9]2[C:14](=[O:15])[NH:13][CH:12]([N:16]([CH2:17][CH2:18][CH2:19][CH3:20])[C:24](=[O:26])[CH3:25])[NH:11][C:10]2=[O:21])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 202879633-(3-Trifluoromethylphenyl)-6-n-butylaminotetrahydro-1,3,5-triazine-2,4-dione

Product 1

HCID 705462633-(3-trifluoromethylphenyl)-6-[(N-acetyl)-n-butylamino]-tetrahydro-1,3,5-triazine-2,4-dioneYield 66%

Procedure

A mixture of 3-(3-trifluoromethylphenyl)-6-n-butylaminotetrahydro-1,3,5-triazine-2,4-dione (4.0 g.) and acetic anhydride (40 ml.) was heated under reflux for 2 hours. The mixture was then distilled at atmospheric pressure over 2 hours, fresh acetic anhydride being added to maintain the original volume. The mixture was then distilled at atmospheric pressure so that the final volume was about 10 ml. Ether (60 ml.) and petroleum ether (b.p. 40°-60° C.) [hereinafter referred to as "40-60 petrol"] (20 ml.) was then added. The white solid which precipitated was washed with ether (2×30 ml.) and air dried to give 3-(3-trifluoromethylphenyl)-6-[(N-acetyl)-n-butylamino]-tetrahydro-1,3,5-triazine-2,4-dione (3.7 g., 66%), m.p. 146°-148° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. distillationThe mixture was then distilled at atmospheric pressure over 2 hours
  4. additionfresh acetic anhydride being added
  5. temperatureto maintain the original volume
  6. distillationThe mixture was then distilled at atmospheric pressure so that the final volume
  7. additionwas then added
  8. customThe white solid which precipitated
  9. washwas washed with ether (2×30 ml.) and air
  10. customdried

Sources & evidence

ORD record
ord-b01d5fb8702549929a31571549411287
Source dataset
uspto-grants-1981_03
Patent number
US04254122

Reaction notes

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