Ammonium Hydroxide → HCID 60165813, compound

HRID 2369330Notes

Reaction equation

HRID 2369330 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([S:12][C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=43)=[C:10]([C:20](OC)=[O:21])[C:9]=2[C:24](OC)=[O:25])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[NH4+].[OH-]>ClCCl.CCOCC.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([S:12][C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=43)=[C:10]([CH2:20][OH:21])[C:9]=2[CH2:24][OH:25])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14923Ammonium HydroxideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 86690035HCID 86690035, compound

Product 1

HCID 60165813HCID 60165813, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of dimethyl 1-(4-fluorophenyl)benzo[d]pyrrolo[2,1-b]thiazole-2,3-dicarboxylate (2.4 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 vacuo. The residue was triturated with ether to give (1-(4-fluorophenyl)benzo[d]pyrrolo[2,1-b]thiazole-2,3-diyl)dimethanol (BO-1592), 1.5 g (76%); mp 155-156° C. 1H NMR (DMSO-d6) δ 4.22 (2H, d, J=5.1 Hz, CH2), 4.66 (2H, d, J=5.1 Hz, CH2), 4.73 (1H, t, J=5.1 Hz, exchangeable, OH), 5.13 (1H, t, J=5.1 Hz, exchangeable, OH), 6.83-6.85 (1H, m, ArH), 7.15-7.19 (2H, m, 2×ArH), 7.37-7.41 (2H, m, 2×ArH), 7.53-7.57 (2H, m, 2×ArH), 7.79-7.81 (1H, m, ArH). Anal. Calcd. for (C18H14FNO2S): C, 66.04; H, 4.31; N, 4.28; S, 9.79. Found: C, 65.25; H, 4.22; N, 4.14; S, 9.76.

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 vacuo
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-7b702f9c4858487fae65fee3fdbd7848
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

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