N-(5-(phenylamino)penta-2,5-dienylidene)aniline monohydrochloride → 4-[2-[6-anilino-1,3,5-hexatrienyl]-3-methyl-5-sulfo-3-(4-sulfobutyl)-3H-1-indoliumyl]-1-butanesulfonate

HRID 508303

反応式

HRID 508303 の反応式
[CH3:1][C:2]1[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:17])=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:20]([OH:23])(=[O:22])=[O:21])[CH:8]=2)[N+:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][S:28]([OH:31])(=[O:30])=[O:29].Cl.[C:33]1([NH:39][CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=NC2C=CC=CC=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(OC(=O)C)(=O)C.C(O)(=O)C>[NH:39]([CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=[CH:1][C:2]1[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:16])=[O:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:20]([OH:23])(=[O:22])=[O:21])[CH:8]=2)[N+:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][S:28]([O-:31])(=[O:29])=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

参加物

4

反応物 2

HCID 73902N-(5-(phenylamino)penta-2,5-dienylidene)aniline monohydrochlorideHCID 584902382,3-dimethyl-5-sulfo-1,3-di(4-sulfobutyl)-3H-indolium

生成物 1

HCID 866953434-[2-[6-anilino-1,3,5-hexatrienyl]-3-methyl-5-sulfo-3-(4-sulfobutyl)-3H-1-indoliumyl]-1-butanesulfonate収率 66.8%

試薬・触媒・溶媒 1

HCID 21895370AcOH AcOAc溶媒

実験手順

300 mg (0.55 mmol) of 2,3-dimethyl-5-sulfo-1,3-di(4-sulfobutyl)-3H-indolium and 190 mg (0.66 mmol) of N-[5-(phenylamino)-2,4-pentadienylidene]aniline monohydrochloride were heated in 6 mL acetic anhydride-acetic acid (1:1, v/v) mixture for 30 min at 110° C. After cooling the product was precipitated with ethyl acetate, filtered off and washed with ether to give 240 mg (56%) of 4-[2-[6-anilino-1,3,5-hexatrienyl]-3-methyl-5-sulfo-3-(4-sulfobutyl)-3H-1-indoliumyl]-1-butanesulfonate. λmax (abs) 505 nm (methanol). This product was used for following step without additional purification.

後処理

  1. temperatureAfter cooling the product
  2. customwas precipitated with ethyl acetate
  3. filtrationfiltered off
  4. washwashed with ether

出典と根拠

ORDレコード
ord-cb08a2ebd89547888a95bf1a38c5ffb1
出典データセット
uspto-grants-2015_08
特許番号
US09095612B2

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