Sodium hydride → 2-amino-5-(Benzothiazol-2-ylmethoxy)-naphthalene

HRID 585598Notes

Reaction equation

HRID 585598 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:10]([OH:14])=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]=1.Br[CH2:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CN(C)C=O.C(OC(=O)C)C>[NH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:14][CH2:16][C:17]2[S:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 902956-AminonaphtholHCID 27762582-(Bromomethyl)-1,3-benzothiazole

Product 1

HCID 223378442-amino-5-(Benzothiazol-2-ylmethoxy)-naphthaleneYield 15%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (1.05 g) is added to a cooled solution of 2-Amino-5-naphthol (4.18 g) in dimethylformamide (100 mL). Stir at room temperature 15 minutes and cool mixture. 2-Bromomethylbenzothiazole (6.00 g) is added and mixture to allowed to warm slowly and stir for 24 hours. Remove dimethylformamide in vacuo. Redilute with ethylacetate and absorb onto silica gel. Chromatograph (ethyl acetate/hexane) to give a brown solid (1.20 g, 15%) which was used directly in the next step., m.p. 141-143° C. 1H NMR (DMSO-d6, 400 MHz): d 5.43 (br s, 2H), 5.69 (s, 2H), 6.72 (d, 1H), 6.80 (s, 1H), 6.95 (d, 1H), 7.12-7.20 (m, 2H), 7.45 (t, 1H), 7.54 (t, 1H), 7.97 (d, 1H), 8.02 (d, 1H), 8.14 (d, 1H). MS [EI, m/z]: 306 [M]+. Anal. Calcd. for C18H14N2OS: C, 70.56; H, 4.61; N, 9.14. Found: C, 70.38; H, 4.42; N, 9.25.

Workup

  1. temperaturecool mixture
  2. temperatureto warm slowly
  3. stirringstir for 24 hours
  4. customabsorb onto silica gel

Sources & evidence

ORD record
ord-c1f8f064938c45a98ca03e770979bd78
Source dataset
uspto-grants-2005_08
Patent number
US06933322B2

Reaction notes

Loading…