Phosphoric Acid → HCID 67336464, compound

HRID 1670554Notes

Reaction equation

HRID 1670554 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[CH2:13][S:14][C:15]1[NH:16][CH:17]=[CH:18][N:19]=1.[P:20](=[O:24])([OH:23])([OH:22])[OH:21]>C(O)C.O>[OH2:21].[P:20]([OH:24])([OH:23])([OH:22])=[O:21].[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[CH2:13][S:14][C:15]1[NH:19][CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 2

HCID 1004Phosphoric AcidHCID 59822278HCID 59822278, compound

Product 1

HCID 67336464HCID 67336464, compoundYield 181.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 7-chloro-6-(1H-imidazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (41.4 g, 140.9 mmol) in absolute ethanol (500 mL) and water (52 mL). Warm to 70° C. to give a solution. Stir the solution at 65 to 70° C. and add 5M phosphoric acid (28.9 mL, 144.5 mmol). Heavy crystallization occurs. Cool to room temperature, then cool to 0 to 5° C. Filter the solid and rinse with cold ethanol. Dry the collected solid in vacuo to obtain the title compound as a white solid (53.7 g, 93%). MS (APCI+) m/z: 294.25 (M+H)+. mp (DSC)=243-245° C.

Workup

  1. customto give a solution
  2. customHeavy crystallization
  3. temperatureCool to room temperature
  4. temperaturecool to 0 to 5° C
  5. filtrationFilter the solid
  6. washrinse with cold ethanol
  7. customDry the collected solid in vacuo

Sources & evidence

ORD record
ord-00723739de5a4294a64f2307fef3d321
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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