Methanol → HCID 20512796, compound

HRID 1164250Notes

Reaction equation

HRID 1164250 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([OH:22])=[C:14]([C:23]([N:25]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:24])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][N:3]=1.[NH2:62][NH2:63].CO>C(Cl)Cl.CC(C)=O>[NH:62]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([OH:22])=[C:14]([C:23]([N:25]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:24])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][N:3]=1)[NH2:63]

Participants

5

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 20512795HCID 20512795, compound

Product 1

HCID 20512796HCID 20512796, compound

Reagents, catalysts & solvents 1

HCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

A mixture of 12.7 g (0.0144 mole) 4-(2-chloro-5-pyridinesulfonamido)-1-hydroxy-N,N-dioctadecyl-2-naphthamide, 4.7 g 95% hydrazine, and 413 ml methanol was heated under reflux for 17 hours. The hot mixture was filtered and then chilled. The product was filtered off, washed first with cold methanol, then with water, and air dried, yielding 11.7 g (93%), mp 96°-8° C. after softening. A thin-layer chromatogram using 85/15 methylene chloride/acetone to elute, showed traces of impurities.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hours
  3. filtrationThe hot mixture was filtered
  4. temperaturechilled
  5. filtrationThe product was filtered off
  6. washwashed first with cold methanol
  7. dry with materialwith water, and air dried
  8. customyielding 11.7 g (93%), mp 96°-8° C. after softening
  9. washto elute

Sources & evidence

ORD record
ord-1c4cc6b6f976486f976278dc4cbc8872
Source dataset
uspto-grants-1983_01
Patent number
US04368249

Reaction notes

Loading…