Hydrogen Sulfide → 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carbothioic acid amide

HRID 1244353Notes

Reaction equation

HRID 1244353 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]#[N:13])[S:11][C:7]=2[C:6]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[SH2:27]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12](=[S:27])[NH2:13])[S:11][C:7]=2[C:6]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 219192224-Methoxy-7-morpholin-4-yl-benzothiazole-2-carbonitrile

Product 1

HCID 219192544-Methoxy-7-morpholin-4-yl-benzothiazole-2-carbothioic acid amideYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.50 g 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carbonitrile and 5.46 ml triethylamine in 13 ml pyridine were stirred for 4 hours with about 5 ml hydrogen sulfide at room temperature. Solvent and excess hydrogen sulfide were removed and the residue chromatographed on siligagel with ethylacetate/heptane 1:1 to yield 0.49 g (87%) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbothioic acid amide; M.p.: 238° C.; MS (ISP): m/e=310 (M+H+).

Workup

  1. customSolvent and excess hydrogen sulfide were removed
  2. customthe residue chromatographed on siligagel with ethylacetate/heptane 1:1

Sources & evidence

ORD record
ord-402ab68cb2ca43c2b92e33d09421f05c
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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