1-Bromo-2-Chloroethane → HCID 68564559, compound

HRID 1927703Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][Cl:10].[CH2:11]([O:18][C:19]1([OH:54])[CH2:32][C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([OH:33])[C:30]([C:42]([N:44]2[CH2:52][C:51]3[C:46](=[CH:47][CH:48]=[C:49]([OH:53])[CH:50]=3)[CH2:45]2)=[O:43])=[CH:29][CH:20]1[C:21]([N:23]([CH2:25][CH2:26][CH2:27][CH3:28])[CH3:24])=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[CH2:11]([O:18][C:19]1([OH:54])[CH2:32][C:31]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)([OH:33])[C:30]([C:42]([N:44]2[CH2:52][C:51]3[C:46](=[CH:47][CH:48]=[C:49]([O:53][CH2:8][CH2:9][Cl:10])[CH:50]=3)[CH2:45]2)=[O:43])=[CH:29][CH:20]1[C:21]([N:23]([CH2:25][CH2:26][CH2:27][CH3:28])[CH3:24])=[O:22])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

235 mg (1.7 mmol) of potassium carbonate and 580 μl (7 mmol) of 1-bromo-2-chloroethane are added to a solution of 400 mg (0.708 mmol) of 2,4-bisbenzyloxy-N-butyl-2,4-dihydroxy-5-(5-hydroxy-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamide in 3 ml of acetonitrile. The suspension is stirred for 16 h at 80° C., cooled to 22° C. and filtered. The residue is washed with acetonitrile, and the combined filtrates are evaporated to dryness in vacuo: 408 mg (92%) of 2,4-bisbenzyloxy-N-butyl-5-[5-(2-chloroethoxy)-1,3-dihydroisoindole-2-carbonyl]-2,4-dihydroxy-N-methylbenzamide (“A10a”), MW 627.2; Rt 2.371 min.

Workup

temperaturecooled to 22° C.
filtrationfiltered
washThe residue is washed with acetonitrile
customthe combined filtrates are evaporated to dryness in vacuo

Sources & evidence

ORD record: ord-63a862146457465091f8f00aa3f66247
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183279B2

Reaction notes

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