Chloromethyl ethyl ether → HCID 66788185, compound

HRID 1045639Notes

Reaction equation

HRID 1045639 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([F:24])([F:23])[F:22])=[C:6]([C:8]2[S:9](=[O:20])(=[O:19])[CH2:10][C:11]3[N:12]=[CH:13][CH:14]=[N:15][C:16]=3[C:17]=2[OH:18])[CH:7]=1.C(N(CC)C(C)C)(C)C.[CH2:34]([O:36][CH2:37]Cl)[CH3:35]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([F:23])([F:24])[F:22])=[C:6]([C:8]2[S:9](=[O:19])(=[O:20])[CH2:10][C:11]3[N:12]=[CH:13][CH:14]=[N:15][C:16]=3[C:17]=2[O:18][CH2:37][O:36][CH2:34][CH3:35])[CH:7]=1

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl ether2×HCID 81531Diisopropylethylamine2×HCID 66789217HCID 66789217, compound2×

Product 1

HCID 66788185HCID 66788185, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7-(5-chloro-2-trifluoromethyl-phenyl)-6,6-dioxo-5,6-dihydro-6-thia-1,4-diaza-naphthalen-8-ol (Compound C7 of Table C) (0.54 g) and N,N-diisopropylethylamine (0.25 ml) in N,N-dimethylformamide (5 ml) under nitrogen atmosphere was added chloromethyl ethyl ether (0.20 ml) and the reaction mixture was stirred at ambient temperature. After 2 hr further diisopropylethylamine (0.10 ml) and chloromethyl ethyl ether (0.10 ml) were added. After a further 3 hours stirring the reaction was concentrated and the residue purified by chromatography on silica gel (eluent: 0-100% v/v ethyl acetate in hexane) to give 7-(5-chloro-2-trifluoromethyl-phenyl)-8-ethoxymethoxy-5H-6-thia-1,4-diaza-naphthalene 6,6-dioxide (0.276 g) 1H-NMR (400 MHz, CDCl3): 1.04 (3H, t), 3.25-3.41 (2H, m), 4.76-4.87 (2H, q), 5.13 (1H, d), 5.33 (1H, d), 7.58-7.61 (2H, m), 7.76 (1H, d), 8.62 (1H, d), 8.73 (1H, d).

Workup

  1. stirringAfter a further 3 hours stirring the reaction
  2. concentrationwas concentrated
  3. customthe residue purified by chromatography on silica gel (eluent: 0-100% v/v ethyl acetate in hexane)

Sources & evidence

ORD record
ord-160727b04b0d4a02978d899edc8d7bac
Source dataset
uspto-grants-2013_10
Patent number
US08569301B2

Reaction notes

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