N-bromobutanimide → HCID 178442369, compound

HRID 1522709Notes

Reaction equation

HRID 1522709 reaction equation
[CH2:1]([C:7]1[CH:8]=[C:9]([C:19]2[C:20]3[NH:24][C:23]([CH:25]=[C:26]4[N:60]=[C:29]([C:30]([C:42]5[CH:47]=[C:46]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH:45]=[C:44]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[CH:43]=5)=[C:31]5[NH:41][C:34](=[CH:35][C:36]6[CH:37]=[CH:38][C:39]=2[N:40]=6)[CH:33]=[CH:32]5)[CH:28]=[CH:27]4)=[CH:22][CH:21]=3)[CH:10]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:61]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH2:13]([C:11]1[CH:10]=[C:9]([C:19]2[C:20]3[NH:24][C:23]([CH:25]=[C:26]4[N:60]=[C:29]([C:30]([C:42]5[CH:43]=[C:44]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[CH:45]=[C:46]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH:47]=5)=[C:31]5[NH:41][C:34](=[C:35]([Br:61])[C:36]6[CH:37]=[CH:38][C:39]=2[N:40]=6)[CH:33]=[CH:32]5)[CH:28]=[CH:27]4)=[CH:22][CH:21]=3)[CH:8]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:12]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 173587012HCID 173587012, compound

Product 1

HCID 178442369HCID 178442369, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a flask containing 1.00 g (1.25 mmol) of 5,15-bis(3,5-dihexylphenyl)porphyrin and 200 mL of chloroform was added 223 mg (1.25 mmol) of N-bromosuccinimide (NBS). After stirring the reaction mixture for 15 min, TLC (hexanes/methylene chloride, 2:1) indicated that the product was present together with lesser amounts of the starting material and the dibrominated porphyrin. The reaction mixture was concentrated to a viscous oil and this material was chromatographed on silica gel (hexanes/methylene chloride, 4:1/3:1) to give 1.116 g (68% yield) of the desired product. 1H NMR (400 MHz) δ−2.97 (2H, s, —NH), 0.93 (12H, t, J=7 Hz, —CH3), 1.36-1.44 (16H, m, —CH2—), 1.48-1.56 (8H, m, —CH2—), 1.83-1.91 (8H, m, —CH2—), 2.89 (8H, t, J=8 Hz, —CH2—), 7.43 (2H, s, Ar—H), 7.85 (4H, s, Ar—H), 8.99 (2H, d, J=4 Hz, β-H), 9.00 (2H, d, J=4 Hz, β-H), 9.28 (2H, d, J=4 Hz, β-H), 9.73 (2H, d, J=5 Hz, β-H), 10.16 (1H, s, meso-H); MALDI-TOF-MS m/z calcd. for C56H69N4Br 876.5, obsd. 876.4; UV/vis (CH2Cl2) 416, 512, 547, 588, 645 (nm).

Workup

  1. concentrationThe reaction mixture was concentrated to a viscous oil
  2. customthis material was chromatographed on silica gel (hexanes/methylene chloride, 4:1/3:1)

Sources & evidence

ORD record
ord-be61b706c801491eaf25403665be366e
Source dataset
uspto-grants-2015_07
Patent number
US09076972B2

Reaction notes

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