Phosphorus oxychloride → HCID 178506080, compound

HRID 1497235Notes

Reaction equation

HRID 1497235 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=3)[NH:10][C:9](=O)[C:8]=2[C:22]2[NH:26][N:25]=[N:24][N:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:29])=O.C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1>[Cl:29][C:9]1[C:8]([C:22]2[NH:26][N:25]=[N:24][N:23]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([F:19])([F:18])[F:20])[CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178518603HCID 178518603, compound

Product 1

HCID 178506080HCID 178506080, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

4-Phenyl-3-(1H-tetrazol-5-yl)-6-trifluoromethyl-1H-quinolin-2-one (160 mg, 448 μmol) was twice co-evaporated with toluene (5 ml). Then toluene (5 ml), phosphorus oxychloride (446 mg, 271 μl, 2.91 mmol) and N,N-diisopropylethylamine (72.3 mg, 97.8 μl, 560 μmol) were added and the mixture was heated to 70° C. for 5 h. Then all volatiles were removed and toluene (5 ml) was added and evaporated twice. Then ethanol (5 ml) was added and evaporated. Water and methanol were added to the remaining residue and the solid was filtered off and dried to obtain the title compound (107 mg, 64%) as brown solid. MS (ESI): 374.3 (M−H)−.

Workup

  1. customThen all volatiles were removed
  2. additiontoluene (5 ml) was added
  3. customevaporated twice
  4. additionThen ethanol (5 ml) was added
  5. customevaporated
  6. additionWater and methanol were added to the remaining residue
  7. filtrationthe solid was filtered off
  8. customdried

Sources & evidence

ORD record
ord-eaf76f982fce4ad9bb5e6118a168ea36
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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