2,4-Difluorophenyl isocyanate → HCID 67442237, compound

HRID 1400835Notes

Reaction equation

HRID 1400835 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:23])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:31])[CH:3]=1.[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[N:40]=[C:41]=[O:42]>C(Cl)Cl>[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[NH:40][C:41]([NH:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([C:22]([N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:23])=[CH:20][CH:21]=4)[S:15][C:8]=23)=[C:4]([F:31])[CH:3]=1)=[O:42]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 58474497HCID 58474497, compound

Product 1

HCID 67442237HCID 67442237, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 126 (125 mg, 0.288 mmol) in DCM (6 mL) was added the 2,4-difluorophenyl isocyanate (134 mg, 0.865 mmol) and the reaction mixture was stirred at RT overnight. The reaction mixture was then concentrated and the resultant solid was triturated with acetone and collected by filtration to give title compound 127 (100 mg, 59% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.37 (s, 1H), 8.61 (s, 1H), 8.51 (d, J=5.48 Hz, 1H), 8.14 (s, 1H), 8.04 (m, 1H), 7.94 (m, 2H), 7.76 (m, 1H), 7.64 (m, 2H), 7.45 (t, J=8.99 Hz, 1H), 7.35 (m, 1H), 7.22 (m, 1H), 7.06 (m, 1H), 6.63 (d, J=5.48 Hz, 1H), 3.48-3.37 (m, 4H), 1.85 (m, 4H). MS (m/z)=589.546 (M+H)

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe resultant solid was triturated with acetone
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-79579528ee3245328831aeb5cfc1a612
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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