Phenol → HCID 18176473, compound

HRID 394452Notes

Reaction equation

HRID 394452 reaction equation
C([CH:8]1[NH:14][CH2:13][CH2:12][S:11][C:10]2[C:15](=[O:20])[N:16]([CH3:19])[N:17]=[CH:18][C:9]1=2)C1C=CC=CC=1.P(=O)(O)(O)O.C1(O)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:19][N:16]1[C:15](=[O:20])[C:10]2[S:11][CH2:12][CH2:13][NH:14][CH2:8][C:9]=2[CH:18]=[N:17]1

Participants

5

Reactant 4

HCID 996PhenolHCID 1004Phosphoric AcidHCID 10340Sodium CarbonateHCID 18176463HCID 18176463, compound

Product 1

HCID 18176473HCID 18176473, compoundYield 72.4%

Conditions

Temperature
150 °C

Procedure

To a solution of 13.10 g (45.5 mmol) 5-benzyl-8-methyl-2,3,4,5-tetrahydro-9(8H)-pyridazino[4,5-b][1,5]thiazepinone in 116 ml of 85% phosphoric acid 5.00 g (53.0 mmol) of phenol are added and the solution is stirred for 3 hours at 150° C. After cooling the solution is poured onto 100 g of ice-water and the pH of the mixture is adjusted to neutral with 138 g of solid sodium carbonate. The precipitate is filtered and the wet filter-cake is boiled with 12×40 ml of isopropanol. The combined isopropanol solutions are evaporated. The residue is triturated with diethyl ether, filtered and washed. In this way 6.50 g (72%) of the title compound are obtained with a melting point of 254-256° C.

Workup

  1. temperatureAfter cooling the solution
  2. filtrationThe precipitate is filtered
  3. filtrationthe wet filter-cake
  4. customThe combined isopropanol solutions are evaporated
  5. customThe residue is triturated with diethyl ether
  6. filtrationfiltered
  7. washwashed

Sources & evidence

ORD record
ord-0255b384caff49918330dfdd82dd23b5
Source dataset
uspto-grants-2003_08
Patent number
US06602865B1

Reaction notes

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