Sodium hydride → HCID 395229, compound

HRID 1174499Notes

Reaction equation

HRID 1174499 reaction equation
[H-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12][C:13]#[N:14].[Cl:15][C:16]1[N:21]=[C:20](Cl)[CH:19]=[CH:18][N:17]=1>C1COCC1>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH:12]([C:18]1[CH:19]=[CH:20][N:21]=[C:16]([Cl:15])[N:17]=1)[C:13]#[N:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 775312,4-DichloropyrimidineHCID 3424652-(1,3-Benzothiazol-2-yl)acetonitrile

Product 1

HCID 395229HCID 395229, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of NaH (60% in oil, 9.2 g, 0.23 mol) in dry THF (200 ml) was added drop wise under inert atmosphere a solution of 1,3-benzothiazol-2yl-acetonitrile (20 g, 0.15 mol) in dry THF (200 ml). After 1 h 30 stirring at r.t., a solution of 2,4-dichloropyri-midine (17.1 g, 0.15 mol) in dry THF (200 ml) was added dropwise. The reaction mixture was allowed to stir under inert atmosphere at r.t. until complete disappearance of the starting material. The reaction was quenched by addition of water and the THF was evaporated. Water was added and the suspension was slightly acidified with aqueous HCl 1M. The precipitate obtained was filtered off and washed thoroughly with water until neutral then with hexane to remove the oil. The crude solid was dried under vacuum at 40° C., affording 28 g (84%) of the title compound as a light brown powder: mp 246° C. dec.; MS: 286.8 (M+1); HPLC (Conditions a, 268 nm) 97%, rt. 5.66 min; 1HNMR (DMSO-d6) δ 13.25 (br s, 1H, exchangeable), 8.09 (d, J=4.14 Hz, 1H), 7.90 (d, J=7.53 Hz, 1H), 7.61 (d, J=7.92 Hz, 1H), 7.39-7.34 (m, 1H), 7.20-7.15 (m, 1H), 6.96 (br d, 1H). CHN analysis: C13H7ClN4S: Calculated: C, 54.19%; H, 2.48%; N, 19.45%. Found: C, 53.35%; H, 2.77%; N, 17.62%.

Workup

  1. customThe reaction was quenched by addition of water
  2. customthe THF was evaporated
  3. additionWater was added
  4. customThe precipitate obtained
  5. filtrationwas filtered off
  6. washwashed thoroughly with water until neutral then with hexane
  7. customto remove the oil
  8. customThe crude solid was dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-97646ec363b54a128cc847d28e38ae3e
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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