Cyclohexyl isothiocyanate → 2-Cyclohexylaminothiocarbonylthioethylamine

HRID 1607095Notes

Reaction equation

[CH:1]1([N:7]=[C:8]=[S:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[NH:17][CH2:18][CH2:19][SH:20])C=CC=CC=1>>[CH:1]1([NH:7][C:8]([S:20][CH2:19][CH2:18][NH2:17])=[S:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 14289Cyclohexyl isothiocyanate

HCID 15616512N-triphenylmethylcysteamine

Product 1

HCID 542301792-Cyclohexylaminothiocarbonylthioethylamine

Procedure

Cyclohexylisothiocyanate (0.2 ml) and N-triphenylmethylcysteamine (150 mg) were subjected to the reaction described in Reference 5. From the reaction product, triphenylmethyl was removed by the method described in Reference 4 to obtain 2-cyclohexylaminothiocarbonylthioethylamine (crude formate: 92 mg). The product was dissolved in anhydrous methanol (2 ml). Triethylamine (0.24 ml) and mitomycin A (97 mg: 0.8 molar equivalent) were added to the reaction solution which was then treated in a similar manner to that described in Example 1 to obtain Compound 37 (54 mg) in the form of grayish blue powders with a yield of 36%.

Workup

customFrom the reaction product, triphenylmethyl was removed by the method

Sources & evidence

ORD record: ord-d9437d75619b443ba16c7a7f7b206621
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863935

Reaction notes

Loading…