Hydrochloric Acid → 1-amino-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)-phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 393368Notes

Reaction equation

HRID 393368 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])=[CH:6][C:5]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([N:29]=C(C)C)[C:19]2=[O:33])=[C:4]([F:34])[CH:3]=1.Cl>CO>[NH2:29][N:20]1[C:21]([C:25]([F:28])([F:26])[F:27])=[CH:22][C:23](=[O:24])[N:18]([C:5]2[CH:6]=[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:15]([O-:17])=[O:16])[C:2]([Cl:1])=[CH:3][C:4]=2[F:34])[C:19]1=[O:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 114206533-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-1-[(1-methylethylidene)-amino]-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Product 1

HCID 113401491-amino-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)-phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneYield 43.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-1-[(1-methylethylidene)-amino]-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.300 g, 0.60 mmol), 1 N HCl (3.0 mL,), and methanol (3.0 mL) was heated to reflux for 2 hours. The reaction was cooled to room temperature, partitioned between water and ethyl acetate, and the phases separated. The aqueous phase was extracted ethyl acetate (3×50 mL) and concentrated. Chromatography (20% ethyl acetate/hexane) of the residue afforded 1-amino-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)-phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 0.12 g (43.5%) of a white solid. 1H-NMR (CDCl3): δ 4.58 (bs, 2H), 6.25 (s, 1H), 6.94 (dd, J=8.38, 1.13 Hz, 1H), 7.03 (d, J=6.52 Hz, 1H), 7.24 (dt, J=7.29, 1.22 Hz, 1H), 7.43 (d, J=8.83 Hz, 1H), 7.53 (dt, J=7.12, 1.69 Hz, 1H), 7.97 (dd, J=8.15, 1.65 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. custompartitioned between water and ethyl acetate
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted ethyl acetate (3×50 mL)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef19b97e9c2b4c628d49861704b4327b
Source dataset
uspto-grants-2004_10
Patent number
US06806367B2

Reaction notes

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