Acetic Anhydride → HCID 15068033, compound

HRID 1031928Notes

Reaction equation

[C:1]([O:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[K+].[Br-].S1C2C=CC=CC=2C(N2CCN(CCCCN3C(=O)C[C:32]4([CH2:36][CH2:35][CH2:34][CH2:33]4)C(O)C3=O)CC2)=N1>>[CH2:36]1[C:35]2([CH2:6][C:5](=[O:7])[O:4][C:1](=[O:3])[CH2:2]2)[CH2:34][CH:33]=[CH:32]1

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 253877Potassium Bromide

HCID 15068025128396-57-6

Product 1

HCID 15068033HCID 15068033, compound

Procedure

Diacid IVe (10.5 g, 57.0 mmol) was dissolved in acetic anhydride (40.0 g, 0.392 mol) and heated to reflux for 15 h. The excess acetic anhydride was distilled off and the resulting oil taken up in a minimum of hot benzene. Slow dilution with hot hexane afforded 8.90 g (two crops, 95%) of IVf as off-white needles, mp 64-5° C.; IR (KBr) 1800, 1770, 1080, 1065, 955 cm-1 ; 1H NMR (CDCl3) δ 5.68 (s, 2H), 2.78 (s, 4H), 2.34 (s, 4H); mass spectrum, m/z (relative intensity) 167 (M+1, 100), 149 (15), 139 (8), 121 (8), 80 (10).

Workup

temperatureheated
temperatureto reflux for 15 h
distillationThe excess acetic anhydride was distilled off
customafforded 8.90 g (two crops, 95%) of IVf as off-white needles, mp 64-5° C.

Sources & evidence

ORD record: ord-5220bbee76f6466fbf5e98c5c46cc0a0
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04956368

Reaction notes

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