Dimethylformamide → HCID 178457774, compound

HRID 1181609Notes

Reaction equation

HRID 1181609 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].CN(C)C=O.C(Cl)(=O)C(Cl)=O.[CH:18]([NH:21][C:22]1[CH:31]=[CH:30][C:25]2[N:26]=[C:27]([SH:29])[S:28][C:24]=2[CH:23]=1)([CH3:20])[CH3:19]>ClCCl.N1C=CC=CC=1>[C:1]([CH2:3][C:4]([N:21]([CH:18]([CH3:20])[CH3:19])[C:22]1[CH:31]=[CH:30][C:25]2[N:26]=[C:27]([SH:29])[S:28][C:24]=2[CH:23]=1)=[O:6])#[N:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 65578Oxalyl chlorideHCID 178456731HCID 178456731, compound

Product 1

HCID 178457774HCID 178457774, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Cyanoacetic acid (1.63 g, 19.17 mmol) was suspended in anhydrous dichloromethane (40 ml). A catalytic amount of N,N-dimethylformamide (0.1 ml) was added and the mixture cooled to 0° C. under an atmosphere of Argon. After 20 minutes stirring at 0° C., oxalyl chloride (1.67 ml, 19.17 mmol) was slowly added to the reaction mixture, which was then allowed to warm to ambient temperature. This mixture was added slowly, after stirring 1 hour, to a 1 M solution of 6-isopropylamino-1,3-benzothiazole-2-thiol (2.16 g, 9.57 mmol) in anhydrous pyridine. After 2 hours the reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and 1 M aqueous citric acid. The resulting precipitate was collected by filtration, combined with the organic extract and concentrated in vacuo. The residue was triturated with diethyl ether to yield 2.32 g (83%). 1H NMR (DMSO-d6) δ=0.98 (m, 6H), 3.43 (s, 2H), 4.75 (sep, 1H), 7.27 (d, 1H), 7.35 (d, 1H), 7.63 (s, 1H), 13.94 (s, 1H); ESIMS: m/z290 (M-H).

Workup

  1. temperatureto warm to ambient temperature
  2. additionThis mixture was added slowly
  3. concentrationAfter 2 hours the reaction mixture was concentrated in vacuo
  4. custompartitioned between ethyl acetate and 1 M aqueous citric acid
  5. filtrationThe resulting precipitate was collected by filtration
  6. extractionorganic extract
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with diethyl ether
  9. customto yield 2.32 g (83%)

Sources & evidence

ORD record
ord-9761d5a1fe044e25bf4698094720d6de
Source dataset
uspto-grants-2007_10
Patent number
US07285562B2

Reaction notes

Loading…