Water → Phenyl (3-(benzyloxy)-4-cyanoisothiazol-5-yl)carbamate

HRID 1712129Notes

Reaction equation

HRID 1712129 reaction equation
[CH2:1]([O:8][C:9](=[NH:25])[C:10]([C:23]#[N:24])=[C:11]([SH:22])[NH:12][C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.BrBr.O>C(#N)C>[C:16]1([O:15][C:13](=[O:14])[NH:12][C:11]2[S:22][N:25]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:10]=2[C:23]#[N:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24408BromineHCID 178511143HCID 178511143, compound

Product 1

HCID 29939179Phenyl (3-(benzyloxy)-4-cyanoisothiazol-5-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. suspension of the adduct, 2-cyano-3-mercapto-3-phenoxycarbonylaminoacrylimidic acid benzyl ester (282 g, 798 mmol) in acetonitrile (2 L) was added pyridine (129 mL, 1.60 mol). Next was added a solution of bromine (41.1 mL, 798 mmol) in acetonitrile (200 mL) over 15 minutes. The reaction was stirred at 0° C. for an additional 1 hour and then at ambient temperature for 2 hour. The mixture was placed in the refrigerator and held at SIC overnight. The solid product was filtered and washed with 0° C. ether (1 L), dried in the same funnel by drawing air through the solid for 4 hours. The solid was added to water (1 L), stirred vigorously for 1 hour, filtered and dried in the same funnel by drawing air through the solid overnight to afford a white solid (320 g pure though still containing some water) that was used, as is, in the next step. 1H NMR (400 MHz, DMSO) δ 5.35 (s, 2H), 7.25-7.45 (m, 10H), 13.20 (broad s, 1H) ppm; MS (APCI, m/z): 350 [M−H]−.

Workup

  1. waitat ambient temperature for 2 hour
  2. customheld at SIC overnight
  3. filtrationThe solid product was filtered
  4. washwashed with 0° C. ether (1 L)
  5. customdried in the same funnel
  6. customfor 4 hours
  7. additionThe solid was added to water (1 L)
  8. stirringstirred vigorously for 1 hour
  9. filtrationfiltered
  10. customdried in the same funnel
  11. customthrough the solid overnight
  12. customto afford a white solid (320 g pure

Sources & evidence

ORD record
ord-86979b543ba745b4b6ac3a077665f46f
Source dataset
uspto-grants-2010_09
Patent number
US07790902B2

Reaction notes

Loading…