Ammonium Hydroxide → HCID 60165812, compound

HRID 2369327Notes

Reaction equation

HRID 2369327 reaction equation
[CH3:1][C:2]1[N:9]2[C:5]([S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)=[C:4]([C:14](OC)=[O:15])[C:3]=1[C:18](OC)=[O:19].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[NH4+].[OH-]>ClCCl.CCOCC.O>[CH3:1][C:2]1[N:9]2[C:5]([S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)=[C:4]([CH2:14][OH:15])[C:3]=1[CH2:18][OH:19]

Participants

8

Reactant 4

HCID 14923Ammonium HydroxideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 60165811HCID 60165811, compound

Product 1

HCID 60165812HCID 60165812, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of dimethyl 1-methylbenzo[d]pyrrolo[2,1-b]thiazole-2,3-dicarboxylate (2.0 g, 6.6 mmol) in anhydrous dichloromethane (30 mL) was added dropwise to a stirred mixture of lithium aluminum hydride (0.6 g, 16.0 mmol) in anhydrous ether (20 mL) at −5° C. to 0° C. The reaction mixture was allowed to stir at this temperature for 20 min. The excess hydride was decomposed by adding water (1 mL) followed by NH4OH (1 mL) and water (1 mL) at −5° C. to 0° C. The mixture was filtered through a pad of Celite, washed with several times with dichloromethane. The combined filtrate and washings were washed successively with water and brine solution. The organic layer was dried (Na2SO4) and concentrated to dryness in vacuum. The residue was triturated with ether to give (1-methylbenzo[d]pyrrolo[2,1-b]thiazole-2,3-diyl) dimethanol (BO-1595), 1.3 g (82%) as white powder; mp 138-139° C. 1H NMR (DMSO-d6) δ 2.63 (3H, s, Me), 4.39 (2H, d, J=5.2 Hz, CH2), 4.56 (2H, d, J=5.2 Hz, CH2), 4.60 (1H, t, J=5.6 Hz, exchangeable, OH), 4.97 (1H, t, J=5.6 Hz, exchangeable, OH), 7.21-7.25 (1H, m, ArH), 7.34-7.38 (1H, m, ArH), 7.76-7.78 (1H, m, ArH), 7.83-7.85 (1H, m, ArH). Anal. Calcd. for (C13H13NO2S): C, 63.13; H, 5.30; N, 5.66; S, 12.97. Found: C, 62.94; H, 5.24; N, 5.83; S, 12.90.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashed with several times with dichloromethane
  3. washThe combined filtrate and washings were washed successively with water and brine solution
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated to dryness in vacuum
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-ac4fde6d26934a6684a98f0f00134b69
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

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