Isocyanate → HCID 131715178, compound
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].[N-:25]=[C:26]=[O:27].[N-:28]=[C:29]=S>>[OH2:23].[O:23]=[C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:24])[N:14]1[CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][NH:1][C:26]([NH:25][CH3:29])=[O:27])[CH:4]=2)[NH:8][CH:7]=1.[O:23]=[C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:24])[N:14]1[CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][NH:1][C:26]([NH:28][CH3:29])=[O:27])[CH:4]=2)[NH:8][CH:7]=1Participants
Procedure
A suspension of 2-[2-[5-(aminomethyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione, hemisulphate, hydrate (1.53 g) in pyridine (50 ml) was cooled in an ice bath and treated dropwise with methylisocyanate (2.5 ml). The mixture was stirred at room temperature for 4 h, and water (15 ml) was added to the resulting white suspension. After 10 min. the yellow solution was acidified with hydrochloric acid (2N), and extracted into ethyl acetate (3×100 ml). The combined organic extract was washed with sodium carbonate solution (2N; 100 ml), dried (magnesium sulphate) and evaporated to dryness, giving a pale yellow solid. On trituration with ether, this afforded the pure title material as a cream crystalline solid (1.22 g) m.p. 210°-212°. The following compounds were similarly prepared from 2[2-[5-(aminomethyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3-(2H)-dione, hemisulphate, hemihydrate and the appropriate isocyanate or isothiocyanate as detailed in Table I.
Sources & evidence
- ORD record
- ord-e37ef19cd4c343d8832423aa4b940433
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04672067
Reaction notes
Loading…