Phosgene → HCID 10115938, compound

HRID 2308505Notes

Reaction equation

HRID 2308505 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]([C:18]3[CH:19]=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=3)[S:16][CH:17]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:32](Cl)(Cl)=[O:33].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>O1CCOCC1.O>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:32]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[O:33])[S:11][C:7]=2[C:6]([C:13]2[N:14]=[C:15]([C:18]3[CH:19]=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=3)[S:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8083MorpholineHCID 8471TriethylamineHCID 22283166HCID 22283166, compound

Product 1

HCID 10115938HCID 10115938, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

0.1 g of 4-methoxy-7-[2-(6-methyl-pyridin-3-yl)-thiazol-4-yl]-benzothiazol-2-ylamine (0.00028 Mol) were dissolved in dioxane (2 ml) and treated with 0.047 ml triethylamine (0.00034 Mol) and 0.164 ml of phosgene (20% in toluene) (0.00031 Mol). After stirring for 2 hrs. at room temperature 0.122 ml of morpholine (0.0014 Mol) were added and the whole mixture was stirred for 16 hrs. at ambient temperature. Upon addition of water (5 ml) a precipitation formed, which was filtered, washed with water and dried. This crude material was triturated with hot MeOH and after cooling to room temperature filtered. The filtrate was evaporated and the residue subjected to column chromatography (silicagel, CH2Cl2/MeOH+1% NH4OH). The title compound was obtained as a light yellow solid (7%); MS (ISP): m/e=468 (M+H+).

Workup

  1. stirringthe whole mixture was stirred for 16 hrs
  2. customat ambient temperature
  3. customa precipitation
  4. customformed
  5. filtrationwhich was filtered
  6. washwashed with water
  7. customdried
  8. customThis crude material was triturated with hot MeOH
  9. filtrationfiltered
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-436e123706bc497b8a501296a3a2d39b
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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