Cyanamide → HCID 11952364, compound

HRID 1669103Notes

Reaction equation

HRID 1669103 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=[O:12])[CH2:7][CH:6]([CH2:14][OH:15])[CH2:5]2.[N:16]#[C:17][NH2:18].[CH]Cl.[OH-].[Na+]>O>[NH2:18][C:17]1[N:16]=[N+:11]([O-:12])[C:10]2[CH:9]=[C:8]3[C:4]([CH2:5][CH:6]([CH2:14][OH:15])[CH2:7]3)=[CH:3][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 9864CyanamideHCID 14798Sodium HydroxideHCID 6432229CID 6432229HCID 25140023HCID 25140023, compound

Product 1

HCID 11952364HCID 11952364, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of nitroaniline 123 (4.43 g, 17.8 mmol) and cyanamide (3.51 g, 83.6 mmol) were mixed together at 100° C., cooled to 50° C., cHCl (8.21 mL) added carefully and the mixture stirred at 65-70° C. for 90 min. A solution of 7.5 M NaOH (72 mL) was added until the mixture was strongly basic and the mixture stirred at 90-98° C. for 45 min. The mixture was cooled, diluted with water (50 mL), filtered, washed with water (3×20 mL) and dried to give 1-oxide 124 (3.67 g, 89%) as a green-yellow solid: mp (DCM/MeOH) 255-257° C.; 1H NMR [(CD3)2SO] δ 7.93 (s, 1H, H-9), 7.33 (s, 1H, H-5), 7.10 (s, 2H, NH2), 4.67 (t, J=5.2 Hz, 1H, OH), 3.40 (dd, J=6.5 Hz, 5.2 Hz, 2H, CH2O), 2.99-3.10 (m, 2H, CH2), 2.73-2.85 (m, 2H, CH2), 2.52-2.63 (m, 1H, CH); 13C NMR [(CD3)2SO] δ 159.9, 153.5, 148.6, 141.9, 128.8, 120.1, 114.1, 63.7, 41.6, 35.3, 34.6. Anal. calcd for C11H12N4O2.¼CH3OH: C, 56.2; H, 5.5; N, 23.3. Found: C, 56.7; H, 5.4; N, 23.2%.

Workup

  1. additionwere mixed together at 100° C.
  2. stirringthe mixture stirred at 90-98° C. for 45 min
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washwashed with water (3×20 mL)
  6. customdried

Sources & evidence

ORD record
ord-8fef15e3e9b14bb5b6332d23d571f429
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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