Methanol → HCID 20283016, compound

HRID 463299Notes

Reaction equation

HRID 463299 reaction equation
CO.[NH2:3][CH2:4][CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[C:9]([C:18](=[O:36])[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:8]=1.C(N(CC)CC)C.ClC(OCC)=O.[C:50](=S)=[S:51]>O>[N:3]([CH2:4][CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[C:9]([C:18](=[O:36])[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:8]=1)=[C:50]=[S:51]

Participants

7

Reactant 5

HCID 887MethanolHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 20283014HCID 20283014, compound

Product 1

HCID 20283016HCID 20283016, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 300 ml of methanol were dissolved 64 g of 4-(2-aminoethyloxy)-2-hexadecylcarbamoyl-1-naphthol and 35 g of triethylamine. To this mixture was added dropwise 19 g of carbon disulfide at a temperature not exceeding 10° C., and the resulting mixture was stirred for 1 hour. Thereafter, 11.9 g of ethyl chloroformate was added dropwise and stirred for additional 30 minutes. The resulting reaction mixture was poured into 1.5 l of water, and precipitated crystals were collected by filtration and recrystallization from acetonitrile to give 47 g of 4-(2-isothiocyanatoethyloxy)-2-hexadecylcarbamoyl-1-naphthol. Yield: 92%. M.P.: 90°-91° C.

Workup

  1. customexceeding 10° C.
  2. stirringstirred for additional 30 minutes
  3. customThe resulting reaction mixture
  4. customprecipitated crystals
  5. filtrationwere collected by filtration and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-421bb7d824604213904abb044a6593e8
Source dataset
uspto-grants-1985_05
Patent number
US04518682

Reaction notes

Loading…