Water → HCID 18952137, compound

HRID 1492216Notes

Reaction equation

HRID 1492216 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:13][CH2:14][O:15][CH3:16])[C:6]1[C:7]([NH2:12])=[CH:8][CH:9]=[CH:10][CH:11]=1.[C:17](Cl)(Cl)=[S:18].O>O1CCOCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:13][CH2:14][O:15][CH3:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]=[C:17]=[S:18]

Participants

5

Reactant 3

HCID 962WaterHCID 10040ThiophosgeneHCID 18952148HCID 18952148, compound

Product 1

HCID 18952137HCID 18952137, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N,N-bis(2-methoxyethyl)benzene-1,2-diamine (7.5 g) in dioxane (10 ml) was added to a mixture of thiophosgene (4 ml) and water (60 ml) which had been cooled to 0° C. The temperature of the mixture was allowed to rise to ambient and the mixture was stirred for 4 hours. Ice water (50 ml) was added and the mixture extracted with ether (3×20 ml). The extract was washed with water (50 ml) and brine (50 ml), dried and evaporated to give a residue which was heated at 45° C. under vacuum (100 mm/Hg) to give 2-[bis(2-methoxyethyl)amino]phenyl isothiocyanate as an oil.

Workup

  1. extractionthe mixture extracted with ether (3×20 ml)
  2. washThe extract was washed with water (50 ml) and brine (50 ml)
  3. customdried
  4. customevaporated
  5. customto give a residue which
  6. temperaturewas heated at 45° C. under vacuum (100 mm/Hg)

Sources & evidence

ORD record
ord-063fd2bed8544e9085aa403c48d27bf0
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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