Hexane → HCID 18183175, compound

HRID 430660Notes

Reaction equation

HRID 430660 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][C:8](=O)[NH:9][N:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25].C(OCC)(=O)C.CCCCCC>N1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][C:8](=[S:25])[NH:9][N:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl Acetate2×HCID 14817Phosphorus sulfide (P2S5)HCID 18183110HCID 18183110, compound

Product 1

HCID 18183175HCID 18183175, compoundYield 172.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

4.3 g of 8-methoxy-1-(4-nitrophenyl)-4,5-dihydro-3H-2,3-benzodiazepin-4-one is mixed in 48 ml of pyridine with 2.46 g of diphosphorus pentasulfide and stirred under argon and with exclusion of moisture for 2 hours at a bath temperature of 100° C. It is diluted with water, and the precipitated product is suctioned off. After chromatography on silica gel first with ethyl acetate:hexane=1:1 and later with ethyl acetate, a total of 3.13 g of 8-methoxy-1-(4-nitrophenyl)-4,5-dihydro-3H-2,3-benzodiazepine-4-thione is obtained.

Sources & evidence

ORD record
ord-c15507d17fa34ef098924cfe730fc7d7
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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