Ethyl isocyanate → 4-(4-Acetylaminophenyl)-1,2-Dihydro-1-Methyl-2-Ethylcarbamoyl-6-Methylthiophthalazine

HRID 48178Notes

Reaction equation

HRID 48178 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([S:21][CH3:22])[CH:19]=3)[CH:14]([CH3:23])[NH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH2:24]([N:26]=[C:27]=[O:28])[CH3:25]>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([S:21][CH3:22])[CH:19]=3)[CH:14]([CH3:23])[N:13]([C:27](=[O:28])[NH:26][CH2:24][CH3:25])[N:12]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 12986172HCID 12986172, compound

Product 1

HCID 129861734-(4-Acetylaminophenyl)-1,2-Dihydro-1-Methyl-2-Ethylcarbamoyl-6-MethylthiophthalazineYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of dihydrophthalazine 8 in chloroform was added ethyl isocyanate (3 eq) at room temperature. The resulting solution was stirred at such temperature for a few days until there is no starting material left from TLC. The solvent was removed under reduced pressure. Purification of the crude product by using a silica gel gave the desired products 9 (Yield: 50%). 1HNMR (CDCl3): 7.70-7.55 (m, 5H), 7.35 (dd, J=4.3 Hz, 1H), 7.19 (m, 2H), 6.53 (br, 1H), 5.73 (q, J=13.2 Hz, 1H), 3.42 (m, 2H), 2.40 (s, 3H), 2.25 (s, 3H), 1.22 (m, 6H).

Workup

  1. waitleft from TLC
  2. customThe solvent was removed under reduced pressure
  3. customPurification of the crude product

Sources & evidence

ORD record
ord-33da16ee21db4d0fa06d2ac97925f03d
Source dataset
uspto-grants-2004_03
Patent number
US06703390B2

Reaction notes

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