Triethylamine → HCID 22283221, compound

HRID 2250733Notes

Reaction equation

HRID 2250733 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([C:13]2[N:14]=[C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[S:16][CH:17]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:31][CH2:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.CN(C1C=CN=CC=1)C.O>[Cl:31][CH2:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:12][C:10]2[S:11][C:7]3[C:6]([C:13]4[N:14]=[C:15]([N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)[S:16][CH:17]=4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)=[O:38])=[CH:35][CH:34]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 516892Sodium BicarbonateHCID 22283186HCID 22283186, compound

Product 1

HCID 22283221HCID 22283221, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

0.165 g of 4-methoxy-7-(2-morpholin-4-yl-thiazol-4-yl)-benzothiazol-2-ylamine (0.00047 Mol) were dissolved in dioxane (5 ml) and combined with 0.1 ml of triethylamine (0.0007 Mol), 0.006 g DMAP (0.000047 Mol) and a solution of 0.116 g of 4-(chlormethyl)benzoylchlorid (0.00062 Mol) in dioxane (1 ml). The reaction mixture was stirred for 6 hrs. at 70° C. After cooling down to room temperature, water (10 ml) and sat. NaHCO3 (10 ml) were added. A precipitation formed. It was filtered, washed with water and tried. This crude product was subjected to column chromatography (silicagel, CH2Cl2/MeOH 19:1). The title compound was obtained as a light yellow solid (65%); F.p.: 166-168° C.

Workup

  1. customat 70° C
  2. customA precipitation
  3. customformed
  4. filtrationIt was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-12404ea23bee4965a6df3b0230512a50
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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