Diphenyl N-Cyanocarbonimidate → HCID 178512236, compound

HRID 507324Notes

Reaction equation

HRID 507324 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[S:8][C:4]=2[CH:3]=1.[CH:12]1[CH:17]=[CH:16][C:15]([O:18][C:19](OC2C=CC=CC=2)=[N:20][C:21]#[N:22])=[CH:14][CH:13]=1>C(#N)C>[C:15]1([O:18][C:19](=[N:1][C:2]2[CH:11]=[CH:10][C:5]3[N:6]=[C:7]([SH:9])[S:8][C:4]=3[CH:3]=2)[NH:20][C:21]#[N:22])[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 178418618HCID 178418618, compound

Product 1

HCID 178512236HCID 178512236, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 200 mL round bottomed flask are added 6-amino-1,3-benzothiazole-2-thiol (2.26 g, 12.4 mmol), diphenylcyanocarbonimidate (4.43 g, 18.6 mmol) and acetonitrile (50 mL). The reaction mixture is refluxed under nitrogen atmosphere for 16 hrs. The precipitates are collected by filtration and washed with acetonitrile (15 mL). Recrystalization of the solid from ethanol affords the intermediate of N-cyano-N′-(2-mercapto-benzothiazol-6-yl)carbamimidic acid phenyl ester as white solid (1.2 g, 30%). 1H NMR (DMSO-d6) δ 7.20-7.42 (m, 8H), 7.78 (s, 1H), 10.88 (b, 1H); ESIMS: m/z 324.8 (M−H).

Workup

  1. temperatureThe reaction mixture is refluxed under nitrogen atmosphere for 16 hrs
  2. filtrationThe precipitates are collected by filtration
  3. washwashed with acetonitrile (15 mL)
  4. customRecrystalization of the solid from ethanol

Sources & evidence

ORD record
ord-1081554857004fb4918d1630861bfc48
Source dataset
uspto-grants-2010_08
Patent number
US07786145B2

Reaction notes

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