Methacryloyl chloride → HCID 19767279, compound

HRID 1590534Notes

Reaction equation

[CH3:1][N:2]([C:15]1[CH:20]=[CH:19][C:18]([N:21]=[N:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[C:32](Cl)(=[O:36])[C:33]([CH3:35])=[CH2:34]>>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([N:22]=[N:21][C:18]2[CH:19]=[CH:20][C:15]([N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:32](=[O:36])[C:33]([CH3:35])=[CH2:34])=[CH:16][CH:17]=2)=[CH:24][CH:25]=1)([O-:31])=[O:30]

Participants

Reactant 2

HCID 13528Methacryloyl chloride

HCID 19767281HCID 19767281, compound

Product 1

HCID 19767279HCID 19767279, compound

Procedure

The 4'-[N-methyl-N-(11-hydroxyundecyl)-amino]-4-nitroazobenzene obtained in process step 1 was reacted with methacryloyl chloride according to the method stated in Example 2, Section 2, to give 4-nitro-4'-[N-methyl-N-(11-methacryloyloxyundec-1-yl)-amino]-azobenzene [methacrylate (A)]. The resulting product had the following physicochemical properties: IR spectrum (KBr pellet): bands at 2,900, 2,850, 1,705, 1,585, 1,490, 1,325, 1,120, 1,150, 1,095, 850 and 810 cm-1 ; 1H nuclear magnetic resonance spectrum (400 MHz, CDCl3, tetramethylsilane as internal standard, chemical shift δ (in ppm): 1.3 to 1.65 (multiplet, 18H), 1.9 (singlet, 3H), 3.1 (singlet, 3H), 3.4 (triplet, 2H), 4.3 (triplet, 2H), 5.6 (singlet, 1H), 6.1 (singlet, 1H), 6.7 (doublet, 2H), 7.9 (doublet, 4H), 8.3 (doublet, 2H); elemental analysis: calculated: 67.3% C, 8.03% H, 13.13% N, 11.25% 0; found: 66.1% C, 7.7% H, 13.8% N, 12.1% 0.

Sources & evidence

ORD record: ord-db06ec8eeeed41039f88a4450518a351
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05204178

Reaction notes

Loading…