Triethylamine → HCID 58811479, compound

HRID 1716381Notes

Reaction equation

HRID 1716381 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:19])[C:5]([NH:8][C:9]([CH3:18])([CH3:17])[CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([C:9]([CH3:17])([CH3:18])[CH2:10][N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:28](=[O:30])[NH:19][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 588114824-Bromo-N1-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-benzene-1,2-diamine

Product 1

HCID 58811479HCID 58811479, compoundYield 139.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Mix 4-bromo-N1-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-benzene-1,2-diamine (3.76 g, 11.5 mmol), triethylamine (4.6 mL, 34.4 mmol) in THF (150 mL). Cool to 0° C. and carefully add solid triphosgene (2.0 g, 6.9 mmol). Allow the reaction to warm to room temperature and stir for 18 h. Cautiously quench the reaction with aqueous K2CO3 and extract into EtOAc. Dry (MgSO4) and concentrate to give 3.4 g yellow solid. Purify by column chromatography using 3% 3N NH3 in MeOH/methylene chloride to give 2.25 g (55%) title compound as a white solid, MS (es) 354, 356 (M+1), 352, 354 (M−1). HPLC(ISO80-10M) t=1.55.

Workup

  1. customthe reaction
  2. temperatureto warm to room temperature
  3. customCautiously quench
  4. customthe reaction with aqueous K2CO3
  5. extractionextract into EtOAc
  6. dry with materialDry (MgSO4)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-5258ec260f2048dc9bba52e666dc2bac
Source dataset
uspto-grants-2010_09
Patent number
US07803814B2

Reaction notes

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