Cyanamide → HCID 25138707, compound

HRID 1669173Notes

Reaction equation

HRID 1669173 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][O:11]2)=[CH:6][C:5]=1[NH2:14])([O-])=[O:2].[N:15]#[C:16][NH2:17].[CH]Cl.[OH-].[Na+]>O>[N+:1]1([O-:2])[C:4]2[CH:13]=[C:12]3[C:7](=[CH:6][C:5]=2[N:14]=[C:16]([NH2:17])[N:15]=1)[CH2:8][CH2:9][CH2:10][O:11]3

Participants

6

Reactant 4

HCID 9864CyanamideHCID 14798Sodium HydroxideHCID 6432229CID 6432229HCID 21827056HCID 21827056, compound

Product 1

HCID 25138707HCID 25138707, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of nitroaniline 238 (2.05 g, 10.6 mmol) and cyanamide (1.78 g, 42.3 mmol) were mixed together at 100° C., cooled to 50° C., cHCl (10 mL) added carefully and the mixture heated at 100° C. for 4 h. The mixture was cooled to 50° C., 7.5 M NaOH solution added until the mixture was strongly basic and the mixture stirred at 100° C. for 3 h. The mixture was cooled, diluted with water (200 mL), filtered, washed with water (3×50 mL) and dried. The aqueous fraction was extracted with CHCl3 (3×50 mL), dried and the solvent evaporated. The combined solids were purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give amine 239 (1.30 g, 56%) as a yellow powder: mp (MeOH/DCM) 280-283° C.; 1H NMR [(CD3)2SO] δ 7.32 (s, 1H, H-10), 7.31 (s, 1H, H-5), 6.96 (br s, 2H, NH2), 4.22 (dd, J=5.3, 5.2 Hz, 2H, H-8), 2.95 (br t, J=6.3 Hz, 2H, H-6), 1.92-1.98 (m, 2H, H-7); 13C NMR [(CD3)2SO] δ 159.1, 152.2, 143.4, 135.8, 128.7, 125.7, 102.6, 66.5, 25.0, 21.0. Anal. calcd for C10H10N4O2: C, 55.0; H, 4.6; N, 25.7. Found: C, 55.1; H, 4.6; N, 25.5%.

Workup

  1. additionwere mixed together at 100° C.
  2. temperaturethe mixture heated at 100° C. for 4 h
  3. temperatureThe mixture was cooled to 50° C.
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. washwashed with water (3×50 mL)
  7. customdried
  8. extractionThe aqueous fraction was extracted with CHCl3 (3×50 mL)
  9. customdried
  10. customthe solvent evaporated
  11. customThe combined solids were purified by chromatography
  12. washeluting with a gradient (0-10%) of MeOH/DCM

Sources & evidence

ORD record
ord-027d6f2cec9543cdb308c54be0c8dc88
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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