O-Phenylenediamine → HCID 58982086, compound

HRID 1182481Notes

Reaction equation

HRID 1182481 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)=[O:12].[NH2:22][C:23]1[S:27][C:26]([SH:28])=[N:25][N:24]=1.[C:29]1(N)C=CC=C[C:30]=1N>>[S:28]=[C:26]1[S:27][C:23]([NH:22][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]([C:2]2[CH:1]=[CH:10][C:5]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:30][CH:29]=3)=[CH:4][CH:3]=2)=[O:12])=[N:24][NH:25]1

Participants

4

Reactant 3

HCID 7243O-PhenylenediamineHCID 109459918-(2-NAPHTHYL)-8-OXOOCTANOIC ACIDHCID 178509208HCID 178509208, compound

Product 1

HCID 58982086HCID 58982086, compoundYield 34%

Procedure

Following the procedure described in Example 22, but substituting carboxylic acid 50h for carboxylic acid 50g and 5-amino-1,3,4thiadiazole-2-thiol for 1,2-phenylenediamine respectively, the title compound 79 was obtained in 34% yield. 1H NMR (300 MHz, 20% CD3OD in CDCl3): δ 7.91 (d, J=8.4 Hz, 2H), 7.58(d, J=8.4 Hz, 2H), 7.52 (m, 2H), 7.38-7.26 (m, 3H), 2.90 (t, J=7.2 Hz, 2H), 2.30 (t, J=7.2 Hz, 2H), 1.62 (m, 4H), 1.30 (m, 4H).

Sources & evidence

ORD record
ord-6d05a59ee092450ba7e5e940b836cb27
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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