Chloromethyl Methyl Ether → HCID 66700250, compound

HRID 2361461Notes

Reaction equation

HRID 2361461 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-5990b01aa6914109b2a7f5a36e81f25d
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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