Acetone → HCID 18768041, compound

HRID 480014Notes

Reaction equation

HRID 480014 reaction equation
Cl.[NH:2]([C:9]1[C:14]([Cl:15])=[CH:13][N:12]=[C:11](Cl)[N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1.CC(C)=O>S1(CCCC1)(=O)=O>[NH:2]([C:9]1[C:14]([Cl:15])=[CH:13][N:12]=[C:11]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 187680474-Anilino-2,5-dichloropyrimidine

Product 1

HCID 18768041HCID 18768041, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
140 °C

Procedure

Ethereal hydrogen chloride (1.0M; 10 ml, 10.0 mmol) was added to a solution of 4-anilino-2,5-dichloropyrimidine (Method 2; 2.41 g, 10.0 mmol) and 4-aminobenzoic acid (1.10 g, 8.0 mmol) in sulpholane (10 ml) and the mixture was heated at 140° C. for 3 hours. The mixture was left to cool and acetone (75 ml) was added. The insoluble solid was collected by filtration and washed with acetone (50 ml) to give the product (2.63 g, 97%). NMR: 7.25 (t, 1H), 7.4 (t, 2H), 7.55-7.65 (m, 4H), 7.7 (d, 2H), 8.35 (s, 1H), 9.6 (br s, 1H), 10.4 (br s, 1H); MS (MH+): 341, 343.

Workup

  1. waitThe mixture was left
  2. temperatureto cool
  3. filtrationThe insoluble solid was collected by filtration
  4. washwashed with acetone (50 ml)

Sources & evidence

ORD record
ord-3ff2d05fcd454941a8c305f1f48bd677
Source dataset
uspto-grants-2003_11
Patent number
US06649608B2

Reaction notes

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