Chloromethyl Methyl Ether → HCID 66700250, compound

HRID 452312Notes

Reaction equation

HRID 452312 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22].[H-].[Na+].C(Cl)OC.C1[CH2:34][O:33][CH2:32][CH2:31]1>>[CH2:32]([O:33][CH2:34][O:20][C:18]1[CH:17]=[CH:16][C:14]2[N:15]=[C:11]([C:10]#[C:9][C:6]3[CH:7]=[CH:8][C:3]([NH:2][CH3:1])=[C:4]([N+:21]([O-:23])=[O:22])[CH:5]=3)[S:12][C:13]=2[CH:19]=1)[CH3:31]

Participants

5

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58362651HCID 58362651, compound

Product 1

HCID 66700250HCID 66700250, compound

Procedure

To a round bottom flask under Ar containing 2-((4-(methylamino)-3-nitrophenyl)ethynyl)benzo[d]thiazol-6-ol (1 equiv) is added THF (5 vol). To this solution is added NaH (1.3 equiv). The solution is stirred at RT for 30 min. To this solution is added MOM-Cl (1.5 equiv). The reaction is stirred overnight at RT. The reaction is poured onto water (10 vol) and extracted into DCM (10 vol). The organic layer is washed with water (10 vol), dried (MgSO4), filtered and concentrated to dryness. The material is purified using EtOAc:Hexanes as the eluent over silica gel to afford the final product.

Workup

  1. stirringThe reaction is stirred overnight at RT
  2. additionThe reaction is poured onto water (10 vol)
  3. extractionextracted into DCM (10 vol)
  4. washThe organic layer is washed with water (10 vol)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe material is purified

Sources & evidence

ORD record
ord-3eecb5fdd31b4a6b8526190b8995a095
Source dataset
uspto-grants-2013_07
Patent number
US08491869B2

Reaction notes

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