O-Toluidine → HCID 178424374, compound

HRID 1770250Notes

Reaction equation

HRID 1770250 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]#[N:10].NC1C(C)=CC=CC=1.[ClH:19].[CH3:20][C:21]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:22]=1[NH2:23]>ClC1C=CC=CC=1>[ClH:19].[CH3:20][C:21]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:22]=1[NH:23][C:9]([NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[NH:10]

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 10261129(2-Methylphenyl)cyanamideHCID 199744032-Methyl-4-nitroaniline hydrochloride

Product 1

HCID 178424374HCID 178424374, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A vigorously stirred mixture of 2-methylphenyl-cyanamide [1.107 g, 0.380 mmol, prepared from o-toluidine by the method of Safter et al. (1948)] and 2-methyl-4-nitroaniline hydrochloride in chlorobenzene (45 ml) was heated at 90° for 3 h and then allowed to cool to 25°. The resulting pale yellow precipitate was collected, washed with CH2Cl2, and dried, giving 2.284 g (91%) of the hydrochloride of the desired product (pure by NMR). A 681 mg sample was recrystallized twice from absolute EtOH to give 600 mg (88%) of the desired product as pale yellow microcrystals suitable for the next reaction: mp 196-200; (CD3OD, 300 MHz) 2.37 (s, 3), 2.47 (s, 3), 7.33-7.40 (m, 4), 7.59 (d, 1), 8.18 (dd, 1), 8.27 (d, 1). A 473 mg sample of the hydrochloride was dissolved in 50 ml of hot water, filtered, cooled to 25°, and treated with 5 ml of 5 N NaOH. The resulting bright yellow precipitate of the title compound (free base) was dried (403 mg, 92%) and then recrystallized twice from 95% EtOH to give the analytical sample as yellow platelets: mp 177-179; (DC3OD, 300 MHz) 2.31 (s, 6), 7.01-7.35 (m, 5), 7.98 (dd, 1), 8.06 (d, 1). Analysis calculated for C15H16N4O2 :C, 63.37; H, 5.67; N, 19.71. Found: C, 63.41; H, 5.42; N, 19.90.

Workup

  1. temperaturewas heated at 90° for 3 h
  2. temperatureto cool to 25°
  3. customThe resulting pale yellow precipitate was collected
  4. washwashed with CH2Cl2
  5. customdried

Sources & evidence

ORD record
ord-f947f1212a194c75813dadbf8da141b1
Source dataset
uspto-grants-1995_01
Patent number
US05385946

Reaction notes

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