Phosphoric Acid → HCID 20145026, compound

HRID 1906017Notes

Reaction equation

HRID 1906017 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14]([C:16]2[S:20][C:19]([NH:21]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:18][C:17]=2[CH3:41])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].OP(O)(O)=O>O>[NH2:21][C:19]1[S:20][C:16]([C:14]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=3)[CH2:11][CH2:12][N:13]=2)=[C:17]([CH3:41])[N:18]=1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 20144993HCID 20144993, compound

Product 1

HCID 20145026HCID 20145026, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methyl-2-tritylamino-5-thiazolecarboxamide (5.0 g) and polyphospholic acid (116% as H3PO4, 50 g) was stirred at 100° C. for 10 hours. After the reaction mixture was cooled, water (250 ml) was added and stirred for 1 hour. After removal of insoluble materials by filtration, the filtrate was neutralized with sodium carbonate. From the aqueous solution was extracted the desired compound with chloroform, and the extract was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was triturated in diisopropyl ether to afford 1-(2-amino-4-methylthiazol-5-yl)-6,7-dimethoxy-3,4-dihydroisoquinoline (0.67 g).

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. stirringstirred for 1 hour
  3. customAfter removal of insoluble materials
  4. filtrationby filtration
  5. extractionFrom the aqueous solution was extracted the desired compound with chloroform
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-73cc14d2f4174adcaa1e35af2ba3d854
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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