Hydrochloric Acid → HCID 178516700, compound

HRID 1769872Notes

Reaction equation

[C:1]([CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:7][CH:6]([N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[C:5]1=[O:32])#[N:2].[N-:33]=[N+:34]=[N-:35].[Na+].Cl.C(N(CC)CC)C.Cl>CN1CCCC1=O>[C:15]1([C:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:4]([CH2:3][C:1]3[NH:35][N:34]=[N:33][N:2]=3)[C:5](=[O:32])[CH:6]([N:21]3[C:22](=[O:31])[C:23]4=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]4[C:25]3=[O:26])[N:7]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 145 °C

Procedure

To a solution of (3RS)-1-cyanomethyl-1,3-dihydro-5-phenyl-3-phthalimido-2H-1,4-benzodiazepin-2-one (100.0 g) and sodium azide (46.4 g) in 1-methyl-2-pyrrolidone (1.74 l) was added triethylamine hydrochloride (49.1 g) under stirring. The mixture was heated on an oil-bath at 145° C. and stirred for 4 hours. The reaction mixture was poured into 5% hydrochloric acid (4.8 l) under cooling and stirring. The resultant precipitate was collected by filtration, washed with water several times and dried in vacuo at 50° C. for 5 hours to afford (3RS)-1,3-dihydro-5-phenyl-3-phthalimido-1-[(1H-tetrazol-5-yl)methyl]-2H-1,4-benzodiazepin-2-one (100.39 g).

Workup

stirringstirred for 4 hours
temperatureunder cooling
stirringstirring
filtrationThe resultant precipitate was collected by filtration
washwashed with water several times
customdried in vacuo at 50° C. for 5 hours

Sources & evidence

ORD record: ord-4f796d97f9f34f6da42e83874085e670
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382664

Reaction notes

Loading…