2-Nitrophenol → HCID 59362999, compound

HRID 2284905Notes

Reaction equation

HRID 2284905 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[N+:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28])([O-:21])=[O:20].C(OCC)(=O)C>CN1C(=O)CCC1.CCCCCC>[Cl:1][C:2]1[N:7]=[C:6]([O:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N+:19]([O-:21])=[O:20])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 69472-NitrophenolHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 59362999HCID 59362999, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2,4,5-trichloropyrimidine (1.3 g, 7.19 mmol) in NMP (3 mL), DIPEA (1.85 g, 14.3 mmol) and 2-nitrophenol (1 g, 7.19 mmol) were added and heated to 100° C. for 1 h. TLC showed completion of starting material (TLC system: 20% ethyl acetate in hexane (Rf): 0.3). The reaction mixture was poured into crushed ice (50 mL). The obtained solid was filtered, washed with water (50 mL) and dried to obtain 2,5-dichloro-4-(2-nitrophenoxy)pyrimidine as an off-white solid. (Yield: 1.7 g, 85%). 1H NMR (400 MHz, D6-DMSO) δ 8.98 (s, 1H), 8.25 (d, 1H), 7.92 (t, 1H), 7.70 (m, 2H).

Workup

  1. additionThe reaction mixture was poured
  2. filtrationThe obtained solid was filtered
  3. washwashed with water (50 mL)
  4. customdried

Sources & evidence

ORD record
ord-e18dff513a9643a582cdb1394e9b774a
Source dataset
uspto-grants-2015_09
Patent number
US09145387B2

Reaction notes

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