Carbon Disulfide → HCID 22766681, compound

HRID 866494Notes

Reaction equation

HRID 866494 reaction equation
[C:1](=[S:3])=[S:2].[C:4]1([CH:10]2[O:14][CH:13]([C:15]([Cl:18])([Cl:17])[Cl:16])[NH:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH3:20]>>[C:4]1([CH:10]2[O:14][CH:13]([C:15]([Cl:18])([Cl:17])[Cl:16])[N:12]([C:1]([S-:3])=[S:2])[CH2:11]2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[CH2:19]([NH+:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH3:20]

Participants

4

Reactant 3

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 234551115-Phenyl-2-(trichloromethyl)-1,3-oxazolidine

Product 1

HCID 22766681HCID 22766681, compound

Procedure

A solution of 355.6g (3.56 moles) triethylamine, 203.6 g (2.68 moles) carbon disulfide, and 474 g (1.78 moles) 5-phenyl-2-trichloromethyloxazolidine (prepared from 2-amino-1-phenyl-ethanol and chloral; m.p. 67°-69°) was stirred for 9 days at ambient temperatures. The solution was removed of volatiles under reduced pressures to leave a residual viscous oil which was extracted with ethyl ether (10 × 200 ml). The combined ether extracts were removed of solvent under reduced pressures to yield 330 g of the crude, liquid triethylammonium 5-phenyl-2-trichloromethyl-3-oxazolidinecarbodithioate.

Workup

  1. customThe solution was removed of volatiles under reduced pressures
  2. customto leave a residual viscous oil which
  3. extractionwas extracted with ethyl ether (10 × 200 ml)
  4. customThe combined ether extracts were removed of solvent under reduced pressures

Sources & evidence

ORD record
ord-eeff751a24d24adc91bf6d0c399594a8
Source dataset
uspto-grants-1978_07
Patent number
US04099003

Reaction notes

Loading…