Trityl chloride → Phenyl [1-methyl-5-(tritylamino)pyrazol-4-yl]carbamate

HRID 459607Notes

Reaction equation

HRID 459607 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10].C(N(CC)CC)C.[C:25]1([C:31](Cl)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCCCCCC>O1CCCC1>[CH3:7][N:6]1[C:2]([NH:1][C:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[C:3]([NH:8][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:4]=[N:5]1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 8900HeptaneHCID 219044605-Amino-1-methyl-4-phenoxycarbonylaminopyrazole

Product 1

HCID 21904567Phenyl [1-methyl-5-(tritylamino)pyrazol-4-yl]carbamateYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-amino-1-methyl-4-phenoxycarbonylaminopyrazole (153.8 g) in tetrahydrofuran (1 L) were added triethylamine (67 g) and triphenylmethyl chloride (185 g) at room temperature. The mixture was stirred for 6.5 hours. To the reaction mixture was added heptane (2.6 L) and the mixture was stirred for 1 hour. The precipitated solid was collected by filtration and washed with heptane-diisopropyl ether (1:1). The crude solid was suspended in water (3 L) and the suspension was stirred for 1 hour. The solid was collected by filtration and dried to give 1-methyl-4-phenoxycarbonylamino-5-triphenylmethylaminopyrazole (253.6 g).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with heptane-diisopropyl ether (1:1)
  4. stirringthe suspension was stirred for 1 hour
  5. filtrationThe solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-357565b0423249bda79dfe4b191372f4
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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