Phenylacetic Acid → 1-(4,5-Dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-phenylethanone

HRID 627830Notes

Reaction equation

[S:1]1[C:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=[CH:2]1.[C:15]1([CH2:21][C:22](O)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[S:1]1[C:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=[C:2]1[C:22](=[O:23])[CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 999Phenylacetic Acid

HCID 579001554,5-Dihydrobenzo[b]thieno[2,3-d]oxepine

Product 1

HCID 579004561-(4,5-Dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-phenylethanone

Procedure

Scheme 7 shows a general method for substitution at the 2-position of 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine intermediates 74 by acylation with a carboxylic acid such as 2-phenylacetic acid to give 1-(4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-phenylethanone intermediate 81. Bromination gives 2-bromo-1-(4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-phenylethanone intermediate 82. Cyclization with a thioamide compound gives 4-(4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-5-phenylthiazole 83.

Sources & evidence

ORD record: ord-6c3a6818da664cac9552c1346df26bbb
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309265B2

Reaction notes

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