Methyl iodide → HCID 23023993, compound

HRID 1373850Notes

Reaction equation

HRID 1373850 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]([NH:17][CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=3)[S:15][CH:16]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4].CI.[CH:31](OC(C)C)(C)C>CN(C)C=O.O>[CH3:31][N:17]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=1)[C:14]1[S:15][CH:16]=[C:12]([C:9]2[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:11][CH:10]=2)[N:13]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7914Diisopropyl EtherHCID 24758Sodium hydride2×HCID 23023970HCID 23023970, compound

Product 1

HCID 23023993HCID 23023993, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under an argon atmosphere, to a suspension of sodium hydride (content 60%, 26.4 g, 0.661 mol) in N,N-dimethylformamide (530 ml, 2.5 v/w) were successively added dropwise a solution of methyl 4-((4-(4-nitrophenyl)-2-thiazolyl)aminomethyl)benzoate (212.4 g, 0.575 mol) obtained in Example 1(2) in N,N-dimethylformamide (743 ml, 3.5 v/w) and methyl iodide (41.2 ml, 0.661 mol) at 10° C. or below, and the mixture was stirred at room temperature for 2 hr. Sodium hydride (content 60%, 2.3 g, 0.057 mol) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was added dropwise to water (2120 ml, 10.0 v/w) at 10° C. or below, and, after stirring at room temperature for 30 min., diisopropyl ether (848 ml, 4.0 v/w) was added and the mixture was stirred for 2 hr. The precipitated crystals were collected by filtration, washed successively with diisopropyl ether (424 ml) and water (424 ml) and dried in vacuo to give the title compound (201.9 g, yield 91.4%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. stirringafter stirring at room temperature for 30 min.
  3. stirringthe mixture was stirred for 2 hr
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed successively with diisopropyl ether (424 ml) and water (424 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fac24893fa3a49f296f7528bf9b3e31a
Source dataset
uspto-grants-2007_01
Patent number
US07163952B2

Reaction notes

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