Dichloromethane → HCID 86701141, compound

HRID 1403086Notes

Reaction equation

HRID 1403086 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:17]=[C:16]([C:18]3[C:27]4[C:22](=[C:23]([C:28]5[CH:29]=[N:30][C:31]6[C:36]([CH:37]=5)=[CH:35][CH:34]=[CH:33][CH:32]=6)[CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][N:19]=3)[CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])[CH2:4][CH2:3]1.[I-].C[CH:40]=[N+:41]=[CH:42]C.[CH2:44](Cl)Cl>>[CH3:40][N:41]([CH2:42][NH:13][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][C:16]([C:18]2[C:27]3[C:22](=[C:23]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][N:19]=2)=[CH:17][C:9]=1[NH:8][CH:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)[CH3:44]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 21892197N,N-dimethylmethyleneammoniumiodideHCID 86701140HCID 86701140, compound

Product 1

HCID 86701141HCID 86701141, compoundYield 95%

Procedure

A solution of compound (6) (0.050 g) and N,N-dimethylmethylene ammonium iodide (0.025 g) in methylene chloride (1 ml) was stirred overnight at room temperature. The reaction solution was partitioned between chloroform and water. The organic layer was neutralized with an aqueous sodium bicarbonate solution, then washed with brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was then purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (38) (0.053 g, 95%) as a pale yellow solid.

Workup

  1. customThe reaction solution was partitioned between chloroform and water
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was then purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-892a08e37b1c49be94c0d49da9409e57
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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