2-Bromoanisole → HCID 4879792, compound

HRID 1678508Notes

Reaction equation

HRID 1678508 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].[N:15]1([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>O.C(Cl)Cl>[Br:6][C:7]1[CH:12]=[C:11]([S:2]([NH:27][C:24]2[CH:23]=[CH:22][C:21]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:26][CH:25]=2)(=[O:5])=[O:3])[CH:10]=[CH:9][C:8]=1[O:13][CH3:14]

Participants

6

Reactant 3

HCID 113582-BromoanisoleHCID 24638Chlorosulfonic acidHCID 75655Benzenamine, 4-(4-morpholinyl)-

Product 1

HCID 4879792HCID 4879792, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To stirred, cold (0 C) chlorosulfonic acid was added 1-bromo-2-methoxy-benzene (1 g) dropwise. The mixture was then allowed to warm to room temp and was stirred for 1 h. The mixture was then cooled again (0 C) and ice was added carefully until no further effervescence was seen. This was further diluted with water and extracted with DCM. The dried extracts were evaporated giving a pale yellow gum. This material was then dissolved in DCM (15 ml) and was treated with 4-morpholin-4-yl-phenylamine (1.43 g) and was stirred for 18 h. The mixture was then evaporated and the residue purified by chromatography. Gradient elution with DCM then DCM:EtOH:NH3; 800:8:1 and finally 400:8:1 gave an off-white solid (1.4 g).

Workup

  1. stirringwas stirred for 1 h
  2. temperatureThe mixture was then cooled again (0 C) and ice
  3. additionwas added carefully until no further effervescence
  4. extractionextracted with DCM
  5. customThe dried extracts were evaporated
  6. customgiving a pale yellow gum
  7. stirringwas stirred for 18 h
  8. customThe mixture was then evaporated
  9. customthe residue purified by chromatography
  10. washGradient elution with DCM

Sources & evidence

ORD record
ord-2c0c5fbba7804a36a85c3441c0943405
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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