Phenyl Isothiocyanate → HCID 59674151, compound

HRID 1391531Notes

Reaction equation

HRID 1391531 reaction equation
C1(N=C=S)C=CC=CC=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+:22]1([CH2:28][CH2:29][N:30]=[C:31]=[N:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:27]COCC1.CNC1[C:42](N)=[CH:43][C:44]([N+:47]([O-:49])=[O:48])=[CH:45]C=1>N1C=CC=CC=1>[CH3:27][N:22]1[C:28]2[CH:42]=[CH:43][C:44]([N+:47]([O-:49])=[O:48])=[CH:45][C:29]=2[N:30]=[C:31]1[NH:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 34200251-N-methyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 59674151HCID 59674151, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of phenyl isothiocyanate (1.58 ml, 13.2 mmol) and 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (6.6 g, 15.6 mmol) was stirred in pyridine (20 ml) at 90° C. After 2 hours, N1-methyl-4-nitro-benzene-1,2-diamine was added and the reaction was heated overnight. The reaction was cooled and concentrated to a red solid. This was dissolved in EtOAc and washed with water. The organic layer was dried over MgSO4 and concentrated to a red solid. This was stirred in MeOH, filtered, and dried to give the title compound as an orange solid (1.97 g, 62%). 1H NMR (300 MHz, d6-DMSO) δ 8.23 (s, 1H), 8.17 (d, J=1.8 Hz, 1H), 8.02 (dd, J=8.7 and 2.1 Hz, 1H), 7.89 (d, J=8.1 Hz, 2H), 7.50 (d, J=8.7 Hz, 1H), 7.36 (m, 2H), 7.02 (m, 1H), 3.79 (s, 1H) ppm. MS (ESI) m/z=269 [M+H]+.

Workup

  1. temperaturethe reaction was heated overnight
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated to a red solid
  4. dissolutionThis was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated to a red solid
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-50b31580183c4d2591118242fa8e607b
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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