Phenyl Isothiocyanate → HCID 708270, compound

HRID 1056267Notes

Reaction equation

HRID 1056267 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:12]1([N:18]=[C:19]=[S:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(O)(C)C>[Br:11][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:2]=1[NH:1][C:19](=[S:20])[N:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]2=[O:6]

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 2702592-Amino-3-bromobenzoic acid

Product 1

HCID 708270HCID 708270, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

TEA (1.93 mL, 13.89 mmol), 2-amino-3-bromo-benzoic acid (Aldrich, 2.00 g, 9.26 mmol), phenyl isothiocyanate (Aldrich; 1.66 mL, 13.89 mmol) were combined in 30 mL t-BuOH, flask sealed, and heated to 100° C. overnight. The heterogeneous reaction was cooled to 40° C. and filtered, rinsing 3× Et2O, and the solid was collected and dried in vacuo to give 8-bromo-3-phenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (3.0 g, 9.00 mmol, 97% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.76 (1H, br. s.), 8.02 (1H, dd, J=7.8, 1.4 Hz), 7.94 (1H, dd, J=7.9, 1.3 Hz), 7.34-7.51 (3H, m), 7.14-7.26 (3H, m). m/z (ESI, +ve) 332.9/334.9 (M+H)+.

Workup

  1. customflask sealed
  2. customThe heterogeneous reaction
  3. temperaturewas cooled to 40° C.
  4. filtrationfiltered
  5. washrinsing 3× Et2O
  6. customthe solid was collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-94f4b13102ce4612a550108ec96a8d08
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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