Triethylamine → HCID 22277828, compound

HRID 1064014Notes

Reaction equation

HRID 1064014 reaction equation
[O:1]=[S:2]1(=[O:29])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH:15][C:16](OCC3C=CC([N+]([O-])=O)=CC=3)=[O:17])[CH:13]=[CH:14][C:3]1=2.[CH2:30]([NH:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1)[CH3:31].C(N(CC)CC)C>CCOC(C)=O.CN(C)C1C=CN=CC=1>[O:29]=[S:2]1(=[O:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH:15][C:16]([N:32]([CH2:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[CH2:30][CH3:31])=[O:17])[CH:13]=[CH:14][C:3]1=2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 96681N-Ethylpyridine-4-methylamineHCID 22277824HCID 22277824, compound

Product 1

HCID 22277828HCID 22277828, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5,5-Dioxo-2-(4-nitrobenzoxycarbonylamino)dibenzothiophene (Example 24; 0.396 g, 1 mmol) was dissolved in EtOAc (10 ml) and treated with 4-(ethylaminomethyl)pyridine (0.150 g, 1.1 mmol), triethylamine (0.202 g, 2 mmol) and 4-(dimethylamino)pyridine (0.006 mg, 0.05 mmol). The reaction was stirred for 18 hours and the suspended solids collected, washed with 1 M aq. NaOH solution, water and then ether to leave the product as a colourless solid. NMR: 9.00 (s, 1H), 8.54 (m, 2H), 8.27 (s, 1H), 7.93 (m, 2H), 7.81 (m, 1H), 7.75 (m, 2H), 7.65 (m, 1H), 7.28 (m, 2H), 4.63 (s, 2H), 3.43 (q, 2H), 1.12 (t, 3H); m/z 394.42

Workup

  1. customthe suspended solids collected
  2. washwashed with 1 M aq. NaOH solution, water

Sources & evidence

ORD record
ord-301023f112474fa580cf410f96a72b7c
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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