Isopropylamine → N-Isopropylbenzamide

HRID 1855618Notes

Reaction equation

[C:1]([NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])C)([CH3:4])([CH3:3])C.[CH:12](N)([CH3:14])[CH3:13].C(N(CC)CC)C.C(Cl)(=O)C1C=CC=CC=1>>[CH:1]([NH:5][C:6](=[O:11])[C:7]1[CH:9]=[CH:14][CH:12]=[CH:13][CH:10]=1)([CH3:3])[CH3:4]

Participants

Reactant 4

HCID 6363Isopropylamine

HCID 7412Benzoyl chloride

HCID 8471Triethylamine

HCID 299326N-tert-Butylpivalamide

Product 1

HCID 79503N-IsopropylbenzamideYield 92%

Procedure

In a fashion similar to the preparation of LtBu,tBuH, treatment of isopropylamine (9.0 mL, 105 mmol) and triethylamine (14.9 mL, 105 mmol) with benzoyl chloride (11.72 mL, 100 mmol) afforded LPh,iPrH as white crystalline solid (15.02 g, 92%) upon crystallization of the crude product from Et2O at −20° C. followed by sublimation at 70° C./0.05 Torr: mp 101-103° C.

Sources & evidence

ORD record: ord-aaa6eaef4344454db1b4d533de618802
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962876B2

Reaction notes

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