Iodine → HCID 11392086, compound

HRID 705479Notes

Reaction equation

[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O=[C:17]([CH:19]=[C:20]([CH3:22])[CH3:21])[CH3:18].II>>[C:4]([O:3][C:1](=[O:2])[NH:8][C:9]1[CH:10]=[C:11]2[C:12](=[CH:13][CH:14]=1)[NH:15][C:20]([CH3:22])([CH3:21])[CH:19]=[C:17]2[CH3:18])([CH3:7])([CH3:6])[CH3:5]

Participants

Reactant 3

HCID 807Iodine

HCID 8858Mesityl oxide

HCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 11392086HCID 11392086, compound

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of N-boc-1,4-phenylene diamine (13.33 g, 63.9mmol) in mesityl oxide (40ml, 367mmol), under an N2 atmosphere, was added iodine (3.47 g, 12.8 mmol) portionwise over 5minutes. The reaction was stirred at 100° C. for 3 hours, then cooled to ambient temperature and reduced to yield the title compound as a crude brown oil (18.4 g, 100%). The product was used without further purification.

Workup

temperaturecooled to ambient temperature

Sources & evidence

ORD record: ord-2ce3e35ad07d4870b91226ac21806724
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174940B2

Reaction notes

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