Water → 20-{3-[N-(4-methylhexahydrophthalimido)amino]-3-oxopropyl}-2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11.2]heneicosane-21-one

HRID 1707310Notes

Reaction equation

HRID 1707310 reaction equation
[NH:1]([C:3](=[O:32])[CH2:4][CH2:5][N:6]1[C:19](=[O:20])[C:9]2([CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[O:8][C:7]21[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[NH2:2].[CH3:33][CH:34]1[CH2:44][CH2:43][CH:37]2[C:38]([O:40][C:41](=O)[CH:36]2[CH2:35]1)=[O:39].O.CCCCC>C1(C)C(C)=CC=CC=1>[CH3:33][CH:34]1[CH2:44][CH2:43][CH:37]2[C:38]([N:2]([NH:1][C:3](=[O:32])[CH2:4][CH2:5][N:6]3[C:19](=[O:20])[C:9]4([CH2:14][C:13]([CH3:15])([CH3:16])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]4)[O:8][C:7]43[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]4)[C:41](=[O:40])[CH:36]2[CH2:35]1)=[O:39]

Participants

6

Reactant 4

HCID 962Water2×HCID 8003PentaneHCID 86876Hexahydro-4-methylphthalic anhydrideHCID 1896313820-(3-Hydrazino-3-oxopropyl)-2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11.2]heneicosane-21-one

Product 1

HCID 1896314120-{3-[N-(4-methylhexahydrophthalimido)amino]-3-oxopropyl}-2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11.2]heneicosane-21-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

The hydrazide of Example 1, 13.5 g (0.03 mole), was added to 225 ml xylene at 75° C. Added dropwise to this was 4-methylhexahydrophthalic anhydride, 5.1 g (0.03 mole) in 25 ml xylene. The apparatus was fitted with a Dean Stark water separation assembly and the reaction mixture was heated to reflux for 4 hours with azeotropic removal of water as it formed. The xylenes were stripped using aspirator vacuum and the residual sticky solid was slurried with 300 ml pentane. The solid was filtered and dried for 2 hours on the filter funnel. The white solid product weighed 11.7 g and had a melting range of 210°-212° C. The infrared spectrum (mull) showed two carbonyl bands at 1690 and 1730 cm-1.

Workup

  1. temperaturethe reaction mixture was heated
  2. customformed
  3. filtrationThe solid was filtered
  4. customdried for 2 hours on the filter funnel

Sources & evidence

ORD record
ord-1ce6e273f96b447ca991dee7f0f7384c
Source dataset
uspto-grants-1994_10
Patent number
US05352719

Reaction notes

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