Triethylamine → HCID 23631175, compound

HRID 33207Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([CH:16]=[N:17][OH:18])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].BrN1C(=O)[CH2:25][CH2:24][C:23]1=O.ClC(C)=C.C(N(CC)CC)C>C(Cl)(Cl)Cl>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([C:16]3[CH:23]=[C:24]([CH3:25])[O:18][N:17]=3)=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 3-Trifluoracetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde oxime (17.2 g) in chloroform (700 ml) was added N-bromosuccinimide (11.8 g), portionwise over 5 min., and the mixture stirred for 1.5 h. 2-Chloropropene (30.3 ml) was added and the reaction cooled to −20° C. Triethylamine (25.1 ml) in chloroform was added over 10 min. and the reaction stirred at room temperature for 18 h. The solution was washed with 2M HCl, dried and evaporated and the residue chromatographed on Si gel, gradient eluting with 10-20% EtOAc in hexane to give the title compound (7.1 g) as a yellow oil.

Workup

stirringthe reaction stirred at room temperature for 18 h
washThe solution was washed with 2M HCl
customdried
customevaporated
customthe residue chromatographed on Si gel
washgradient eluting with 10-20% EtOAc in hexane

Sources & evidence

ORD record: ord-bbd9b97bd8104ef59a7aed5071746cad
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429579B2

Reaction notes

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