Methyl iodide → HCID 19703219, compound

HRID 861446Notes

Reaction equation

HRID 861446 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][S:12]([CH:15]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:16]([NH:18][CH:19]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)[C:20]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21])=[O:17])(=[O:14])=[O:13].[C:43]([O-])([O-])=O.[K+].[K+].IC.ClCl>CN(C)C=O.O>[CH3:43][N:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[S:12]([CH:15]([CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:16]([NH:18][CH:19]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]#[N:35])=[CH:32][CH:33]=1)[C:20]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21])=[O:17])(=[O:14])=[O:13]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24526ChlorineHCID 19703225HCID 19703225, compound

Product 1

HCID 19703219HCID 19703219, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2 g of compound 4 are dissolved in 20 ml of dimethylformamide at 0° C. and 0.475 g of K2CO3 and 0.214 ml of ICH3 are added. After 24 hours at 5° C., 20 ml of H2O and 40 ml of CH2 Cl2 are added. The organic phase decanted is washed, dried and concentrated to dryness. The residue is recrystallized from (CH3)2CHOH to give 1.76 g of final product which melts at 186° C.

Workup

  1. customThe organic phase decanted
  2. washis washed
  3. customdried
  4. concentrationconcentrated to dryness
  5. customThe residue is recrystallized from (CH3)2CHOH

Sources & evidence

ORD record
ord-3a2c671039e74217b83d081b6973022f
Source dataset
uspto-grants-1998_02
Patent number
US05714497

Reaction notes

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