Methyl Bromide → HCID 19098325, compound

HRID 1975684Notes

Reaction equation

HRID 1975684 reaction equation
[C:1]([NH:11][CH2:12][C:13]([NH:15][C:16]1[S:17][C:18]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:19][N:20]=1)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:29][O-].[Na+].CBr>CO.O>[C:1]([NH:11][CH2:12][C:13]([N:15]=[C:16]1[N:20]([CH3:29])[N:19]=[C:18]([S:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[S:17]1)=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

6

Reactant 3

HCID 6323Methyl BromideHCID 10942334Sodium MethoxideHCID 19098303HCID 19098303, compound

Product 1

HCID 19098325HCID 19098325, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of the product from Example VIII (ca 30 gm, 0.1 mole) in methanol (200 ml)m containing sodium methoxide (from 2.5 g sodium, 0.11 mole) is warmed in a flask fitted with a Dry Ice condenser, stirred 3 hr., then cooled to 5° C. Methyl bromide gas was then passed through the reaction (0.15 mole) and the solution stirred overnight at room temperature. The solution is diluted with water (200 ml) to give a sticky solid, ca25 gm. this is slurried with cold concentrated sodium hydroxide solution to remove starting material Yield 20 gm, 40%, recrystallized from ethanol, 15 gm, m.p. 92° C.

Workup

  1. temperatureis warmed in a flask
  2. customfitted with a Dry Ice condenser
  3. stirringthe solution stirred overnight at room temperature
  4. customto give a sticky solid, ca25 gm
  5. customthis is slurried with cold concentrated sodium hydroxide solution to remove
  6. customrecrystallized from ethanol, 15 gm, m.p. 92° C.

Sources & evidence

ORD record
ord-0570e2c7a95c47eba66dbab9a3746d0f
Source dataset
uspto-grants-1994_02
Patent number
US05288735

Reaction notes

Loading…