Methanol → HCID 22603059, compound

HRID 1271316Notes

Reaction equation

HRID 1271316 reaction equation
[AlH4-].[Li+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17](OCC)=[O:18])=[CH:15][CH:14]=1.C(Cl)Cl.CO>C1COCC1.O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]1[CH:23]=[CH:22][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 28112Lithium aluminum hydrideHCID 22603049HCID 22603049, compound

Product 1

HCID 22603059HCID 22603059, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium tetrahydroaluminate (0.1107 mol) in THF (100 ml) was added dropwise at 0° C. under N2 flow to a suspension of ethyl 4-(2-benzothiazolylamino)benzoate (0.1107 mol) in water. The mixture was brought to RT and stirred for 30 minutes. The mixture was hydrolized by adding water (8 ml) dropwise and then CH2Cl2 (50 ml), and a little CH3OH was added. The precipitate was filtered and the solvent was evaporated. The residue was crystallized from 2-propanone and DIPE. The precipitate was filtered off and dried, yielding 8 g (86%) of 4-(2-benzothiazolylamino)benzenemethanol (interm. 8).

Workup

  1. customwas brought to RT
  2. filtrationThe precipitate was filtered
  3. customthe solvent was evaporated
  4. customThe residue was crystallized from 2-propanone and DIPE
  5. filtrationThe precipitate was filtered off
  6. customdried

Sources & evidence

ORD record
ord-7ad608953c73499ea2b25e9cc8871584
Source dataset
uspto-grants-2007_04
Patent number
US07205312B2

Reaction notes

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