N-Methylaniline → HCID 59851164, compound

HRID 545012Notes

Reaction equation

HRID 545012 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7](=[O:18])[CH2:8][C:9]3[CH:14]=[N:13][C:12](S(C)=O)=[N:11][C:10]=3[C:4]=2[CH:3]=1.[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7](=[O:18])[CH2:8][C:9]3[CH:14]=[N:13][C:12]([N:22]([CH3:21])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:11][C:10]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 66934698HCID 66934698, compound

Product 1

HCID 59851164HCID 59851164, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 10-bromo-2-methanesulfinyl-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (100 mg) was stirred with N-methyl aniline (1 mL) and refluxed overnight at 150° C. Water was added and the product was extracted with methylene chloride, dried over MgSO4, filtered and concentrated. Purification by C-18 RP LC-MS chromatography afforded I-85 (10%): MS m/z=395 (M+H).

Workup

  1. extractionthe product was extracted with methylene chloride
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by C-18 RP LC-MS chromatography
  6. customafforded I-85 (10%)

Sources & evidence

ORD record
ord-1a96dda44da842f189da3877318d0117
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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