Ammonia → HCID 22742009, compound

HRID 1057701Notes

Reaction equation

HRID 1057701 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl.C(N(CC)CC)C.Cl[CH2:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][C:31]=1[CH2:32]Cl)[NH2:28].[N:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41]2[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:44](=O)[NH:43][N:42]=2)=[CH:36][CH:35]=1.CN(C)C(=O)N(C)C.N>O.ClCCl>[CH3:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][C:31]=1[CH3:32])[NH:28][C:44]1[C:45]2[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:41]([CH2:40][C:37]2[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=2)=[N:42][N:43]=1

Participants

9

Reactant 6

HCID 222AmmoniaHCID 11130Triethylamine hydrochlorideHCID 12437TetramethylureaHCID 14812Phosphorus oxide (P4O10)HCID 7899544-(4-Pyridylmethyl)-1(2H)-phtalazinoneHCID 57011945HCID 57011945, compound

Product 1

HCID 22742009HCID 22742009, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 1.80 g (12.68 mmol) phosphorus pentoxide, 1.73 g (12.6 mmol) triethylamine hydrochloride, and 1.529 g (12.6 mmol) 3,4-dichloromethylaniline is heated and stirred in a nitrogen atmosphere at 200° C. until a homogeneous melt has formed. To the melt, 1 g (4.2 mmol) of 4-(4-pyridylmethyl)-1(2H)-phthalazinone (for preparation see German Auslegeschrift no. 1 061 788 [published 23.07.1959]) is added and the mixture stirred for 4 h at 200° C. After slight cooling, 4 ml tetramethylurea is added to the reaction mixture, followed by 2 ml water at about 120° C. The solution obtained is then distributed between dichloromethane and a mixture of 20 ml water and 5 ml conc. ammonia, and the organic phase dried over anhydrous sodium sulfate, filtered and evaporated under vacuum. Double recrystallization of the residue from acetonitrile and drying under HV (8 h, 120° C.) yields title compound; m.p. 180-181° C.; ESI-MS: (M+H)+=341.

Workup

  1. temperatureis heated
  2. customhas formed
  3. stirringthe mixture stirred for 4 h at 200° C
  4. customThe solution obtained
  5. dry with materialthe organic phase dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customDouble recrystallization of the residue from acetonitrile
  9. customdrying under HV (8 h, 120° C.)

Sources & evidence

ORD record
ord-d7030e9a1cb940c08a263a19d1e90e27
Source dataset
uspto-grants-2003_02
Patent number
US06514974B2

Reaction notes

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