s-1,3-Benzothiazol-2-yl benzenecarbothioate → 2,2-Bis{4-[2-benzoyloxy-3-(7,7,9,9-tetramethyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl)propoxy]cyclohexyl}propane

HRID 1758201

Reaction equation

HRID 1758201 reaction equation
[OH:1][CH:2]([CH2:39][N:40]1[C:49]([CH3:51])([CH3:50])[CH2:48][C:43]2([O:47][CH2:46][CH2:45][O:44]2)[CH2:42][C:41]1([CH3:53])[CH3:52])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([CH:14]2[CH2:19][CH2:18][CH:17]([O:20][CH2:21][CH:22]([OH:38])[CH2:23][N:24]3[C:33]([CH3:35])([CH3:34])[CH2:32][C:27]4([O:31][CH2:30][CH2:29][O:28]4)[CH2:26][C:25]3([CH3:37])[CH3:36])[CH2:16][CH2:15]2)([CH3:13])[CH3:12])[CH2:7][CH2:6]1.[C:54](SC1SC2C=CC=CC=2N=1)(=[O:61])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>C1C=CC=CC=1>[C:54]([O:1][CH:2]([CH2:39][N:40]1[C:41]([CH3:53])([CH3:52])[CH2:42][C:43]2([O:47][CH2:46][CH2:45][O:44]2)[CH2:48][C:49]1([CH3:51])[CH3:50])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([CH:14]2[CH2:19][CH2:18][CH:17]([O:20][CH2:21][CH:22]([O:38][C:54](=[O:61])[C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[CH2:23][N:24]3[C:33]([CH3:35])([CH3:34])[CH2:32][C:27]4([O:28][CH2:29][CH2:30][O:31]4)[CH2:26][C:25]3([CH3:37])[CH3:36])[CH2:16][CH2:15]2)([CH3:12])[CH3:13])[CH2:7][CH2:6]1)(=[O:61])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

4

Reactant 2

HCID 270394s-1,3-Benzothiazol-2-yl benzenecarbothioateHCID 205106002,2-Bis{4-[2-hydroxy-3-(7,7,9,9-tetramethyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl)propoxy]cyclohexyl}propane

Product 1

HCID 205105622,2-Bis{4-[2-benzoyloxy-3-(7,7,9,9-tetramethyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl)propoxy]cyclohexyl}propane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.5 g of 2,2-bis{4-[2-hydroxy-3-(7,7,9,9-tetramethyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl)propoxy]cyclohexyl}propane and 1.2 g of 2-benzoylthiobenzthiazole were refluxed in 30 ml of anhydrous benzene for 4.5 hours. After completion of the reaction, the reaction mixture was treated with an aqueous alkali and then extracted with benzene, giving crystals. The crystals were purified by column chromatography through silica gel eluted with a 4:1 by volume mixture of diethyl ether and ethyl acetate. The desired Compound No. 222 was obtained in the form of a white powder melting at 77°-79° C.

Workup

  1. customAfter completion of the reaction
  2. additionthe reaction mixture was treated with an aqueous alkali and
  3. extractionthen extracted with benzene
  4. customgiving crystals
  5. customThe crystals were purified by column chromatography through silica gel
  6. washeluted with a 4:1 by volume mixture of diethyl ether and ethyl acetate

Sources & evidence

ORD record
ord-915f9cc3d87843bab679e9efbedb4fe3
Source dataset
uspto-grants-1983_02
Patent number
US04371644

Linked notes

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