4-Methylphenyl isocyanate → HCID 9950716, compound

HRID 1171033Notes

Reaction equation

HRID 1171033 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1.[C:18]1([CH3:27])[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1>ClCCl>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:25]([NH:24][C:21]4[CH:22]=[CH:23][C:18]([CH3:27])=[CH:19][CH:20]=4)=[O:26])=[CH:7][CH:6]=3)=[CH:9][O:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 59794225HCID 59794225, compound

Product 1

HCID 9950716HCID 9950716, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. suspension of Example 13E (50 mg, 0.22 mmol) in dichloromethane (3 mL) was treated with p-tolylisocyanate (0.031 mL, 0.24 mmol), warmed to room temperature, and stirred overnight. The resulting precipitate was collected by vacuum filtration, washed with dichloromethane, and dried to provide 55 mg (70%) of the desired product. MS (ESI(+)) m/e 360 (M+H)+; 1H NMR (DMSO-d6) δ 8.80 (s, 1H), 8.60 (s, 1H), 8.25 (s, 1H), 7.92 (s, 1H), 7.6 (d, J=8.4 Hz, 2H), 7.43 (d, J=8.7 Hz, 2H), 7.35 (d, J=8.4 Hz, 2H), 7.10 (d, J=8.1 Hz, 2H), 6.52 (br s, 2H), 2.25 (s, 3H); Anal. Calcd. for C20H17N5O2: C, 66.84; H, 4.77; N, 19.49. Found: C, 66.58; H, 4.65; N, 19.42.

Workup

  1. filtrationThe resulting precipitate was collected by vacuum filtration
  2. washwashed with dichloromethane
  3. customdried

Sources & evidence

ORD record
ord-7db3185eb0a74d309162b14fedf1aa7b
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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