Hydrochloric Acid → HCID 13314917, compound

HRID 325849Notes

Reaction equation

HRID 325849 reaction equation
[C:1]([O:7][CH2:8]Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:10][N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[SH:16].Cl>C1COCC1>[CH3:10][N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[S:16][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 87885Chloromethyl pivalateHCID 178480602HCID 178480602, compound

Product 1

HCID 13314917HCID 13314917, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.53 g (0.01 mole) of pivalyloxymethyl chloride dissolved in 30 ml of THF was added 1.14 g (0.01 mole) of 1-methyl-2-mercaptoimidazole. The clear yellow solution that resulted was stirred at room temperature overnight. The solution was concentrated to give a glass which was triturated twice with 100 ml of ether. The suspension was filtered and the residue was dried to give 1.85 g (mp 128°-132°, 67% yield) of the desired product as its hydrochloride. IR (KBr) 2800-2200 cm-1 ; (broad, s) (N+H), 1730 cm-1 (s) (C=O) and 1870 and 1820 cm-1 ; 1H NMR (CDCl3) δ7.60 (broad s, 2, N--CH=CH--N), 5.85 (s, 2, CO2CH2S), 3.57 (s, 3, N--CH3) and 1.18 (s, 9, (CH3)3C).

Workup

  1. customThe clear yellow solution that resulted
  2. concentrationThe solution was concentrated
  3. customto give a glass which
  4. customwas triturated twice with 100 ml of ether
  5. filtrationThe suspension was filtered
  6. customthe residue was dried

Sources & evidence

ORD record
ord-43c20c8452b14a6c8a73509c5bc9637e
Source dataset
uspto-grants-1984_04
Patent number
US04443435

Reaction notes

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