Morpholine → HCID 18356993, compound

HRID 427288Notes

Reaction equation

HRID 427288 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([Br:11])=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[C:5]=2[N:6]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>O1CCCC1>[Br:11][C:10]1[C:4]2[S:3][C:2]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:6][C:5]=2[C:7]([O:12][CH3:13])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 18356994354760-28-4

Product 1

HCID 18356993HCID 18356993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2,7-dibromo-4-methoxybenzothiazole (1.8 g) and morpholine (10 ml) in tetrahydrofuran (10 ml) was heated at 80° C. for 2 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was dried over magnesium sulphate (3 g), filtered and the filtrate evaporated in vacuo to yield an off white solid. This was purified by recrystallisation from ethyl acetatelhexane to yield the title compound as a white solid (1.2 g). TLC Rf 0.39 (50% ethyl acetate in hexane).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate (3 g)
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. customto yield an off white solid
  7. customThis was purified by recrystallisation from ethyl acetatelhexane

Sources & evidence

ORD record
ord-7d4636cf4b354785b9610c1928f972ff
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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