3,4-Dimethoxyaniline → HCID 12622371, compound

HRID 1905785Notes

Reaction equation

HRID 1905785 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[CH3:12][S-:13](C)[C:14](=[N:16][C:17]#[N:18])[S-]>>[C:17]([NH:16][C:14](=[N:6][C:5]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[S:13][CH3:12])#[N:18]

Participants

3

Reactant 2

HCID 227703,4-DimethoxyanilineHCID 178503843HCID 178503843, compound

Product 1

HCID 12622371HCID 12622371, compound

Procedure

South African OPI specification No. 79/1059 describes a process for the production of 4-amino-6,7-dimethoxy-2-[4-(furo-2-yl)-piperazin-1-yl]-quinazoline (prazosin), in which 3,4-dimethoxyaniline is reacted with S,S-dimethyl-N-cyanodithioimidocarbonate to form N-cyano-N'-(3,4-dimethoxyphenyl)-S-methylisothiourea which is then condensed with 1-(furo-2-yl)-piperazine to form 4-(furo-2-yl)-piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]-carboximide amide which, in turn, is closed at 180° C. to form the 4-amino-6,7-dimethoxy-2-[4-(furo-2-yl)-piperazin-1-yl]-quinazoline ring.

Sources & evidence

ORD record
ord-9cded1f74de2490c8eca96b05fa97deb
Source dataset
uspto-grants-1987_03
Patent number
US04647684

Reaction notes

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