Benzo(d)thiazol-2-amine → HCID 15086004, compound

HRID 635858Notes

Reaction equation

HRID 635858 reaction equation
C([O:3][C:4]([C:6]1[N:13]2[C:9]([S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=32)=[N:8][CH:7]=1)=O)C.NC1SC2C=CC=CC=2N=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:8]1[CH:7]=[C:6]([CH2:4][OH:3])[N:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[S:10][C:9]=12

Participants

5

Reactant 3

HCID 8706Benzo(d)thiazol-2-amineHCID 10890197HCID 10890197, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15086004HCID 15086004, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of imidazo[2,1-b]benzothiazole-3-carboxylic acid ethyl ester (Formula J-1), (synthesized from 2-aminobenzothiazole by a modification of the procedures described by Fajeli et al., Heterocycles, 1986, 24, 379) (4.5 g) in THF (75 mL) was treated with LiAlH4 (0.91 g) and reacted for 5.25 hours. The suspension was quenched by serial additions of water and 15% sodium hydroxide. The suspension was diluted with THF and filtered. The filtrate was evaporated, the residue was triturated with hexane to yield imidazo[2,1-b]benzothiazole-3-methanol (Formula J-2) (2.77 g, 74%). Crude imidazo[2,1-b]benzothiazole-3-methanol (Formula J-2) was used without further purification.

Workup

  1. customreacted for 5.25 hours
  2. customThe suspension was quenched by serial additions of water and 15% sodium hydroxide
  3. additionThe suspension was diluted with THF
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue was triturated with hexane

Sources & evidence

ORD record
ord-8312ea30ccbc4a19a959fcdae9488630
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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