Triethylamine → HCID 20308604, compound

HRID 1763904Notes

Reaction equation

HRID 1763904 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[F:8][C:9]([F:27])([F:26])[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:17]=[C:16]([I:24])[C:15]=1[OH:25])=[O:11].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][N:2]([CH3:7])[S:3](=[O:5])(=[O:4])[O:25][C:15]1[C:16]([I:24])=[CH:17][C:18]([C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:19][C:14]=1[CH2:13][NH:12][C:10](=[O:11])[C:9]([F:8])([F:26])[F:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 20308602HCID 20308602, compound

Product 1

HCID 20308604HCID 20308604, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,N-dimethylsulfamoyl chloride (17.4 g., 0.12 mole) in dry methylene chloride (75 ml.) maintained under a nitrogen atmosphere is added slowly and with good stirring a solution of 2,2,2-trifluoro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)phenylmethyl]acetamide (8 g., 0.02 mole) and triethylamine (12.12 g., 0.12 mole) in dry methylene chloride (200 ml.) at 20°-25° C. The resulting reaction mixture is stirred at 20°-25° C. under nitrogen for 72 hours. Removal of the solvent in vacuo leaves a tacky residue which is partitioned between ether and water. The phases are separated and the organic phase is washed successively with 2N hydrochloric acid, water and saturated brine, dried over sodium sulfate and filtered. Evaporation of the filtrate leaves the intermediate 2-(2,2,2-trifluoroacetamidomethyl)-4-(1,1-dimethylethyl)-6-iodophenyl N,N-dimethylsulfamate as a tan oil (10.3 g., 100%).

Workup

  1. additionis added slowly
  2. customThe resulting reaction mixture
  3. customRemoval of the solvent in vacuo
  4. customleaves a tacky residue which
  5. customis partitioned between ether and water
  6. customThe phases are separated
  7. washthe organic phase is washed successively with 2N hydrochloric acid, water and saturated brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-2201c12b345042dc843858e0e21ff9b2
Source dataset
uspto-grants-1978_09
Patent number
US04113877

Reaction notes

Loading…