Acetic Anhydride → HCID 135675003, compound

HRID 1198197Notes

Reaction equation

[OH:1][CH:2]([C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)[CH2:3][NH:4][C:5](=[O:29])[C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[C:22]([CH3:27])[NH:21][C:20]3=[O:28])[CH2:13][C:14]#[CH:15])=[CH:8][CH:7]=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>>[C:39]([O:1][CH:2]([C:30]1[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=1)[CH2:3][NH:4][C:5](=[O:29])[C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[C:22]([CH3:27])[NH:21][C:20]3=[O:28])[CH2:13][C:14]#[CH:15])=[CH:8][CH:7]=1)(=[O:41])[CH3:40]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 135674995HCID 135674995, compound

Product 1

HCID 135675003HCID 135675003, compoundYield 88%

Procedure

Using an analogous procedure to that described in Example 4, N-[2-hydroxy-2-(4-nitrophenyl)ethyl]-p-[N-(2-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl)-N-(prop-2-ynyl)amino]benzamide was reacted with acetic anhydride to give N-[2-acetoxy-2-(4-nitrophenyl)ethyl]-p-[N-(2-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl)-N-(prop-2-ynyl)amino]benzamide (containing 2.3 equivalents of water) in 88% yield, m.p. 198°-203° C.

Sources & evidence

ORD record: ord-e6b49aa4bb5d452795dd324752c82231
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05280027

Reaction notes

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