Isopropyl chloroformate → HCID 178449782, compound

HRID 2240328Notes

Reaction equation

HRID 2240328 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][NH:4][C:5]1[CH:14]=[CH:13][C:8]2[N:9]=[C:10]([SH:12])[S:11][C:7]=2[CH:6]=1.C(N(CC)C(C)C)(C)C.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>CC(C)=O>[SH:12][C:10]1[S:11][C:7]2[CH:6]=[C:5]([N:4]([CH2:3][CH:2]([CH3:15])[CH3:1])[C:26](=[O:27])[O:28][CH:29]([CH3:31])[CH3:30])[CH:14]=[CH:13][C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 178448785HCID 178448785, compound

Product 1

HCID 178449782HCID 178449782, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a 50 ml round bottomed flask were added 6-[(2-methylpropyl)amino]-1,3-benzothiazole-2-thiol (100 mg, 0.42 mmol), acetone (10 ml), N,N-diisopropylethylamine (54.2 mg, 0.42 mmol) and isopropyl chloroformate (51.5 mg, 0.42 mmol). The reaction mixture was stirred for 10 h, filtered, and the solid that was obtained was triturated with diethyl ether to afford 30 mg (59%) of the title compound. 1H NMR (DMSO-d6) δ=0.80 (d, 6H), 1.11 (d, 6H), 1.60 (m, 1H), 3.43 (d, 2H), 4.76 (m, 1H), 7.24 (br s, 2H), 7.60 (s, 1H); ESIMS: m/z 323 (M−H).

Workup

  1. filtrationfiltered
  2. customthe solid that was obtained
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-cd1b308a98ba47fa9b8c120c100c5da2
Source dataset
uspto-grants-2010_05
Patent number
US07723366B2

Reaction notes

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