Triethylamine → HCID 13279416, compound

HRID 2296413Notes

Reaction equation

HRID 2296413 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[Cl:8][C:9]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:10]=1[O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:24]([O-:26])=[O:25])=[C:16]([CH:23]=1)[C:17]([O:19][CH2:20][CH2:21][OH:22])=[O:18].C(N(CC)CC)C>CCOCC>[Cl:8][C:9]1[CH:30]=[C:29]([C:31]([F:33])([F:32])[F:34])[CH:28]=[CH:27][C:10]=1[O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:24]([O-:26])=[O:25])=[C:16]([CH:23]=1)[C:17]([O:19][CH2:20][CH2:21][O:22][S:3](=[O:5])(=[O:4])[N:2]([CH3:7])[CH3:1])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 13259764HCID 13259764, compound

Product 1

HCID 13279416HCID 13279416, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Dimethylsulfamoyl chloride (7.2 g, 0.05 mole) was added dropwise to a solution of 2-hydroxyethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (10 g, 0.025 mole), triethylamine (10 ml) and ethyl ether (200 ml). The mixture was heated to and held at reflux for 5 hrs., cooled, added 200 ml of ether and washed three times with water. The ethereal solution was dried over MgSO4, concentrated to 13.9 g of yellow gum. The gummy material was run through a silica gel with 30% acetone-70% cyclohexane as eluent to afford 3.0 g of pure 2-(N,N-dimethylsulfamoyloxy)ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate as colorless gum; nmr (CDCl3) 2.96 (S, 6H), 3.84 (m, 2H), 4.52 (m, 2H), 6.88-8.24 (m, 6H).

Workup

  1. temperatureThe mixture was heated to and
  2. temperatureat reflux for 5 hrs
  3. temperature, cooled
  4. washwashed three times with water
  5. dry with materialThe ethereal solution was dried over MgSO4
  6. concentrationconcentrated to 13.9 g of yellow gum

Sources & evidence

ORD record
ord-e499412d585447d0b3c96af79eb92746
Source dataset
uspto-grants-1984_01
Patent number
US04429146

Reaction notes

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