Aluminium lithium hydride → N-[6-(Aminomethyl)-1,3-benzothiazol-2-yl]-N'-ethylurea

HRID 9174

Reaction equation

HRID 9174 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]2[N:7]=[C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])[S:9][C:5]=2[CH:4]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>COCCOC>[NH2:2][CH2:1][C:3]1[CH:17]=[CH:16][C:6]2[N:7]=[C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])[S:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21985533N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-ethylurea

Product 1

HCID 21985534N-[6-(Aminomethyl)-1,3-benzothiazol-2-yl]-N'-ethylurea

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

About 0.05 g of N-(6-cyano-1,3-benzothiazol-2-yl)-N′-ethylurea was charged into about 10 mL of ethyleneglycol dimethylether. Introduced about 50 mg lithium aluminum hydride in several portions over about 12–24 hours. The slurry was quenched with about 5–10 mL ethyl acetate then about 1–2 mL of saturated aqueous sodium sulfate. The slurry was then diluted with water and extracted with ethyl acetate. Following drying and removal of solvents under reduced pressure, the product was isolated by preparative HPLC. 1H NMR 1.08 (t, 3H), 1.88 (s, 3H), 3.17 (m, 2H), 3.83 (s, 2H), 7.07 (m, 1H), 7.32 (m, 1H), 7.54 (d, 1H), 7.8 (s, 1H); LC/MS 1.86 min, 251 (M+1), 249 (M−1).

Workup

  1. customThe slurry was quenched with about 5–10 mL ethyl acetate
  2. additionThe slurry was then diluted with water
  3. extractionextracted with ethyl acetate
  4. customFollowing drying
  5. customremoval of solvents under reduced pressure
  6. customthe product was isolated by preparative HPLC
  7. customLC/MS 1.86 min, 251 (M+1), 249 (M−1)

Sources & evidence

ORD record
ord-032960dec0b94b21ba18a8f769a61520
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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