Phenyl isocyanate → Phenylurea

HRID 631507Notes

Reaction equation

HRID 631507 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1OC)[N:9]=[CH:8][N:7]=C2OC1C=C(C=CC=1)N.C1(N=C=[O:31])C=CC=CC=1>C1COCC1>[C:10]1([NH:9][C:8](=[O:31])[NH2:7])[CH:5]=[CH:4][CH:3]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 498410023-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline

Product 1

HCID 6145PhenylureaYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-(6,7-dimethoxyquinazolin-4-yloxy)aniline from Example 113A (89 mg, 0.3 mmol) in THF (3 mL) was added phenyl isocyanate (33 uL, 0.3 mmol) and the solution stirred at room temperature overnight. The reaction was concentrated in vacuo, diluted with EtOAc, and filtered to give 14346,7-dimethoxyquinazolin-4-yloxy)phenyl)-3-phenylurea (63 mg, 0.15 mmol, 50%). 1H NMR (300 MHz, DMSO-d6) δ 8.88 (s, 1H), 8.74 (s, 1H), 8.57 (s, 1H), 7.61-7.56 (m, 2H), 7.48-7.35 (m, 4H), 7.32-7.21 (m, 3H), 7.02-7.89 (m, 2H), 3.99 (s, 6H); LC-MS (ESI) m/z 417 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d8111ead98a34ab68e9e1f0e7921dd8b
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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