3-Nitrophenol → Heptadecyl carbamic acid 3-nitrophenyl ester

HRID 1110322Notes

Reaction equation

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

Participants

Reactant 2

HCID 111373-Nitrophenol

HCID 135601031-Isocyanatoheptadecane

Product 1

HCID 67787655Heptadecyl carbamic acid 3-nitrophenyl ester

Procedure

Using this procedure heptadecyl isocyanate was treated with 3-nitrophenol to give heptadecyl carbamic acid 3-nitrophenyl ester (mp 66°-73°, Anal. Calcd for C24H40N2O4 : C, 68.54; H, 9.59; N, 6.66. Found: C, 68.44; H, 9.88; N, 6.41) which was hydrogenated to give heptadecylcarbamic acid 3-aminophenyl ester (mp 69°-75°, Anal. Calcd for C24H42N2O4 : C, 73.80; H, 10.84; N, 7.17. Found: C, 73.79; H, 11.08; N, 6.84).

Sources & evidence

ORD record: ord-64b18b58d81b4d7890d96ef798bf2c4d
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05324747

Reaction notes

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