Water → HCID 54752976, compound

HRID 1983845Notes

Reaction equation

[CH2:1]1[CH2:11]CN2C(=NCCC2)CC1.[Br:12][C:13]1[CH:14]=[C:15]([C:19]([C:21]2[CH:26]=[C:25]([CH3:27])[C:24]([Cl:28])=[CH:23][C:22]=2[OH:29])=O)[CH:16]=[CH:17][CH:18]=1.C([CH:32]([CH2:36][C:37](Cl)=[O:38])[C:33](Cl)=[O:34])C.[OH2:40]>C(#N)C>[CH2:11]([O:40][C:37](=[O:38])[CH2:36][C:32]1[C:33](=[O:34])[O:29][C:22]2[C:21]([C:19]=1[C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Br:12])[CH:14]=1)=[CH:26][C:25]([CH3:27])=[C:24]([Cl:28])[CH:23]=2)[CH3:1]

Participants

Conditions

Temperature: 30 °C

Procedure

DBU (211 ml) was added to a solution of (3-bromophenyl) (4-chloro-2-hydroxy-5-methylphenyl)methanone (170 g) in acetonitrile (510 ml) at 25 to 30° C. Then, a solution of ethyl succinic chloride (146 g) in acetonitrile (340 ml) was added dropwise over 30 minutes at 25 to 40° C. After the drop was completed, the mixture was stirred at 30° C. for 1 hour. Water (94 ml) was added dropwise keeping the reaction solution at 25 to 30° C. After the mixture was stirred at the same temperature for 1 hour, the resulting crystals were filtered, and washed with a mixture of acetonitrile and water (9/1, 170 ml) four times, dried under reduced pressure to obtain the title compound (174 g, yield 76.7%).

Workup

customat 25 to 30° C
stirringAfter the mixture was stirred at the same temperature for 1 hour
filtrationthe resulting crystals were filtered
washwashed with a mixture of acetonitrile and water (9/1, 170 ml) four times
customdried under reduced pressure

Sources & evidence

ORD record: ord-3e8f19f522cd4c56b4b8ec5deeab5cb2
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541478B2

Reaction notes

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