Phthalic Anhydride → HCID 178444740, compound

HRID 1635766Notes

Reaction equation

HRID 1635766 reaction equation
C1(=O)OC(=[O:5])C2=CC=CC=C12.[NH2:12][C:13]1[N:18]=[C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:16]=[C:15]([Cl:26])[N:14]=1.S([O-])(O)=O.[Na+].[OH-].[Na+]>C(O)(C)C.C(OC(C)C)(C)C.O>[NH2:12][C:13]1[N+:18]([O-:5])=[C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:16]=[C:15]([Cl:26])[N:14]=1

Participants

8

Reactant 4

HCID 6811Phthalic AnhydrideHCID 14798Sodium HydroxideHCID 111837886-Chloro-N4-hexyl-2,4-pyrimidinediamineHCID 23665763Sodium Bisulfite

Product 1

HCID 178444740HCID 178444740, compoundYield 42.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
22.5 °C

Procedure

5.95 g of urea/H2O2 complex and 9.07 g of phthalic anhydride were suspended in 90 ml of isopropanol, in a three-necked flask. The mixture was stirred for 30 min at room temperature (20-25° C.). 10 g of 2-amino-4-hexylamino-6-chloropyrimidine were then added while controlling the exotherm at +30° C. After reaction for 3 hours, 100 ml of sodium hydrogen sulfite were poured thereinin to destroy the residual oxidizing agents. The mixture was permitted to separate out by settling and the upper phase was concentrated under vacuum. The residue obtained was taken up in a water (80 ml)/30% sodium hydroxide (20 ml) mixture. The solid obtained was reimpasted in 150 ml of isopropyl ether. The solid was filtered off and washed. It was dried in a heated desiccator. 4.52 g of the expected compound were thus obtained, for a yield of 42%.

Workup

  1. customat +30° C
  2. customAfter reaction for 3 hours
  3. customto destroy the
  4. customto separate out
  5. concentrationthe upper phase was concentrated under vacuum
  6. customThe residue obtained
  7. customThe solid obtained
  8. filtrationThe solid was filtered off
  9. washwashed
  10. customIt was dried in a heated desiccator

Sources & evidence

ORD record
ord-a56f5114d8044557b618d21df28f6115
Source dataset
uspto-grants-2003_01
Patent number
US06511659B2

Reaction notes

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