Diisopropylethylamine → HCID 178449632, compound

HRID 1640038Notes

Reaction equation

HRID 1640038 reaction equation
C[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.[CH:16](N(CC)C(C)C)(C)C.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)=[O:27]>CC(C)=O>[SH:12][C:10]1[S:11][C:7]2[CH:6]=[C:5]([N:4]([CH:3]([CH3:16])[CH2:2][CH3:15])[C:26](=[O:27])[O:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[CH:14]=[CH:13][C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 178448785HCID 178448785, compound

Product 1

HCID 178449632HCID 178449632, compoundYield 48%

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 4-chlorophenyl chloroformate (78.8 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 38 mg (48%) of the title compound. 1H NMR (DMSO-d6) δ=0.85 (d, 6H), 1.70 (m, 1H), 3.53 (br s, 2H), 7.12 (d, 2H), 7.31 (d, 1H), 7.41 (m, 3H), 7.79 (s, 1H); ESIMS: m/z 393 (M+H).

Workup

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

Sources & evidence

ORD record
ord-65943fe9cd5d486299f27598a9509740
Source dataset
uspto-grants-2012_02
Patent number
US08110686B2

Reaction notes

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