5-Bromoisatoic Anhydride → 7-Bromo-4-(2,4-dimethoxybenzyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

HRID 351840Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])O[C:7](=[O:12])[C:6]=2[CH:13]=1.[CH3:14][O:15][C:16]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:17]=1[CH2:18][NH:19][CH2:20]C(O)=O>CC1C=CC(C)=CC=1>[CH3:14][O:15][C:16]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:17]=1[CH2:18][N:19]1[C:7](=[O:12])[C:6]2[CH:13]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[NH:10][C:9](=[O:11])[CH2:20]1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 6-bromo-2H-3,1-bezoxazine-2,4(1H)-dione (22.0 g, 91 mmol) containing (2,4-dimethoxy-benzylamino)-acetic acid (22.5 g, 100 mmol) in p-xylene (200 mL) was heated under reflux (150° C.) for 1 h. After cooling to room temperature the precipitate was filtered off and washed with p-xylene (100 ml). Yield: 33.5 g (91%) m/z 403/405 (M).

Workup

temperaturewas heated
temperatureAfter cooling to room temperature the precipitate
filtrationwas filtered off
washwashed with p-xylene (100 ml)

Sources & evidence

ORD record: ord-fe179141732e462b91e0f789298484f1
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743789B2

Reaction notes

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