Ammonium Hydroxide → HCID 60165814, compound

HRID 2369333Notes

Reaction equation

HRID 2369333 reaction equation
[Cl: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>[Cl: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 86690037HCID 86690037, compound

Product 1

HCID 60165814HCID 60165814, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of dimethyl 1-(4-chlorophenyl)benzo[d]pyrrolo[2,1-b]thiazole-2,3-dicarboxylate (2.1 g, 5.0 mmol) in anhydrous dichloromethane (30 mL) was added dropwise to a stirred mixture of lithium aluminum hydride (0.45 g, 12.5 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-chlorophenyl)benzo[d]pyrrolo[2,1-b]thiazole-2,3-diyl)dimethanol (BO-1582), 1.5 g (88%); mp 151-152° C. 1H NMR (DMSO-d6) δ 4.22 (2H, d, J=4.4 Hz, CH2), 4.66 (2H, d, J=4.4 Hz, CH2), 4.76 (1H, t, J=5.2 Hz, exchangeable, OH), 5.14 (1H, t, J=5.2 Hz, exchangeable, OH), 6.91-6.93 (1H, m, ArH), 7.16-7.22 (2H, m, 2×ArH), 7.53 (2H, d, J=8.4 Hz, 2×ArH), 7.61 (2H, d, J=8.4 Hz, 2×ArH), 7.79-7.82 (1H, m, ArH). Anal. Calcd. for (C18H14ClNO2S): C, 62.88; H, 4.10; N, 4.07; S, 9.33. Found: C, 62.73; H, 4.09; N, 4.06; S, 9.19.

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-709087157b594f26adc25af77911be2d
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

Loading…