Phenoxycarbonyl isothiocyanate → HCID 178511143, compound

HRID 1712128Notes

Reaction equation

HRID 1712128 reaction equation
[CH2:1]([O:8][C:9](=[NH:13])[CH2:10][C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:14]([C:21]([N:23]=[C:24]=[S:25])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[CH2:1]([O:8][C:9](=[NH:13])[C:10]([C:11]#[N:12])=[C:24]([SH:25])[NH:23][C:21]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12212046Phenoxycarbonyl isothiocyanateHCID 299391912-Cyano-acetimidic acid benzyl ester

Product 1

HCID 178511143HCID 178511143, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred 0° C. solution of 2-cyano-acetimidic acid benzyl ester (327 g, 1.88 mol) in acetonitrile (1 L) was added a 0° C. solution of phenoxycarbonylisothiocyanate (353 g, 1.97 mol) in acetonitrile (1 L). The reaction was allowed to warm to ambient temperature and was stirred overnight. The mixture was then placed in the refrigerator and kept still at 5° C. for 48 hours. The solid product was filtered, compressed, and washed with 20° C. acetonitrile (3×200 mL). Air was then drawn though the relatively stable solid followed by further drying under high vacuum to yield a yellow solid (282 g, 798 mmol, 42%). 1H NMR (400 MHz, DMSO) δ 5.39 (s, 2H), 7.11-7.19 (m, 2H), 7.20-7.24 (m, 1H), 7.36-7.46 (m, 7H), 10.23 (broad s, 1H), 10.67 (s, 1H), 12.19 (broad s, 1H) ppm; MS (APCI, m/z): 354 [M+H]+.

Workup

  1. waitkept still at 5° C. for 48 hours
  2. filtrationThe solid product was filtered
  3. washwashed with 20° C. acetonitrile (3×200 mL)
  4. customby further drying under high vacuum

Sources & evidence

ORD record
ord-7c98cbc5c642410c976627312c2705f6
Source dataset
uspto-grants-2010_09
Patent number
US07790902B2

Reaction notes

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