Triethylamine → 1-Benzyloxy-3-[2-[(diethoxyphosphoryl)acetyl]hydrazino]-7-trifluoromethylquinoxalin-2(1H)-one

HRID 744013Notes

Reaction equation

HRID 744013 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10](Cl)=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[CH2:13]([O:20][N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=2)[N:24]=[C:23]([NH:35][NH2:36])[C:22]1=[O:37])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>O1CCCC1>[CH2:13]([O:20][N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]([F:32])([F:33])[F:34])[CH:29]=2)[N:24]=[C:23]([NH:35][NH:36][C:10](=[O:11])[CH2:9][P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:1][CH3:2])=[O:5])[C:22]1=[O:37])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10822542(Diethoxyphosphoryl)acetyl chlorideHCID 194214071-Benzyloxy-3-hydrazino-7-trifluoromethylquinoxalin-2(1H)-one

Product 1

HCID 194214131-Benzyloxy-3-[2-[(diethoxyphosphoryl)acetyl]hydrazino]-7-trifluoromethylquinoxalin-2(1H)-oneYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (diethoxyphosphoryl)acetyl chloride (5.8 g, 27 mmol) in 40 ml of dry tetrahydrofuran was added to a solution of 1-benzyloxy-3-hydrazino-7-trifluoromethylquinoxalin-2(1H)-one (8.75 g, 25 mmol) and dry triethylamine (3.6 ml, 27 mmol) in 200 ml of dry tetrahydrofuran. The mixture was stirred at room temperature for 3 h and filtered. The filtrate was evaporated to dryness, and the residue was crystallized by trituration with water (200 ml) to give 12.85 g (97%) of the title compound. M.p. 163°-166° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. customthe residue was crystallized by trituration with water (200 ml)

Sources & evidence

ORD record
ord-0d5a73708da046b4a7ebdae40a8ce315
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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