Phenyl Isothiocyanate → HCID 53955336, compound

HRID 620399Notes

Reaction equation

HRID 620399 reaction equation
C(N(CC)CC)C.Cl.[NH:9]=[C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=[CH:11]1.[C:22]1([N:28]=[C:29]=[S:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[C:16]1([N:13]2[CH:14]=[CH:15][C:10](=[N:9][C:29](=[S:30])[NH:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]=[N:12]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 21246174HCID 21246174, compound

Product 1

HCID 53955336HCID 53955336, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.3 g (52.4 millimoles) of triethylamine were added dropwise to 10.0 g (48.2 millimoles) of 1,4-dihydro-4-imino-1-phenylpyridazine hydrochloride in 20 ml (22.6 g, 167 millimoles) of phenyl isothiocyanate at room temperature, while stirring. After the addition was complete, the reaction mixture was stirred for a further 2 hours at room temperature and then diluted with 30 ml of acetone. The product was filtered off under suction, washed with acetone, with water and again with acetone, and recrystallized from ethanol. 6.0 g (41% of theory) of 1,4-dihydro-1-phenyl-4-[(phenylthiocarbamyl)-imino]-pyridazine were isolated as orange crystals of melting point 171°-173° C.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for a further 2 hours at room temperature
  3. filtrationThe product was filtered off under suction
  4. washwashed with acetone, with water and again with acetone
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-dbe3183e83704c509f2b66b8bc5e9428
Source dataset
uspto-grants-1989_04
Patent number
US04820821

Reaction notes

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