(2,4-Dimethoxy-benzylamino)-acetic acid → 4-(2,4-Dimethoxy-benzyl)-7-methylsulfanyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

HRID 351848Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:14]=[CH:13][C:6]2[NH:7][C:8](=[O:12])O[C:10](=[O:11])[C:5]=2[CH:4]=1.[CH3:15][O:16][C:17]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:18]=1[CH2:19][NH:20][CH2:21]C(O)=O>CC1C=CC(C)=CC=1>[CH3:15][O:16][C:17]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:18]=1[CH2:19][N:20]1[C:10](=[O:11])[C:5]2[CH:4]=[C:3]([S:2][CH3:1])[CH:14]=[CH:13][C:6]=2[NH:7][C:8](=[O:12])[CH2:21]1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 6-methylsulfanyl-1H-benzo[d][1,3]oxazine-2,4-dione (4.8 g, 23 mmol) containing (2,4-dimethoxy-benzylamino)-acetic acid (5.6 g, 25 mmol) in p-xylene (50 mL) was heated under reflux (150° C.) for 3 h. After cooling to room temperature the precipitate was filtered off and washed with p-xylene (2×20 ml). Yield: 7.5 g (89%). m/z 373 (MH+).

Workup

temperaturewas heated
temperatureAfter cooling to room temperature the precipitate
filtrationwas filtered off
washwashed with p-xylene (2×20 ml)

Sources & evidence

ORD record: ord-3268e0dbcb094314921dcf8f61690392
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743789B2

Reaction notes

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