Thionyl Chloride → HCID 135744185, compound

HRID 1828120Notes

Reaction equation

HRID 1828120 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[C:7]3[N:39]=[C:38]4[N:40]=[C:31]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=54)[N:30]=[C:28]4[NH:29][C:21]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=54)=[N:20][C:18]4=[N:19][C:11]([C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=54)=[N:10][C:9]=2[NH:8]3)[CH:6]=1.[Cl:41][S:42]([OH:45])(=O)=[O:43].S(Cl)([Cl:48])=O>O>[CH:2]1[CH:1]=[CH:6][C:5]2[C:4](=[C:9]3[N:10]=[C:11]4[N:19]=[C:18]([C:17]5[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=54)[N:20]=[C:21]4[NH:29][C:28]([C:27]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=54)=[N:30][C:31]4=[N:40][C:38]([C:37]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=54)=[N:39][C:7]=2[NH:8]3)[CH:3]=1.[S:42]([Cl:41])([Cl:48])(=[O:45])=[O:43]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 86280045Phthalocyanine3×

Product 1

HCID 135744185HCID 135744185, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
77.5 °C

Procedure

An unsubstituted metallic phthalocyanine compound is added by small portions in three times to ten times amount (by weight) of chlorosulfonic acid while maintaining at 18° C. or less. After stirring at that temperature for 1 hour, the temperature is increased at a rate of 0.5 to 1° C. per minute, and the mixture is reacted at a temperature of 130 to 135° C. for from 4 to 6 hours. Thereafter, the mixture was cooled to 70 to 85° C., thionyl chloride in an amount of twice to six times the amount of the unsubstituted metallic phthalocyanine is added dropwise while maintaining at from 70 to 80° C. over 10 to 15 hours. After stirring for several hours at that temperature, the mixture was cooled to 15 to 20° C. and continuously stirred for from 10 to 15 hours. The reaction mixture is discharged by small portions into iced water in an amount of 50 times to 200 times the amount of the metallic phthalocyanine. The resulting deposit is filtrated and washed with iced water until becoming neutral, followed by drying, to obtain a metallic phthalocyanine sulfonylchloride.

Workup

  1. temperaturewhile maintaining at 18° C. or less
  2. temperaturethe temperature is increased at a rate of 0.5 to 1° C. per minute
  3. customthe mixture is reacted at a temperature of 130 to 135° C. for from 4 to 6 hours
  4. temperaturewhile maintaining at from 70 to 80° C. over 10 to 15 hours
  5. stirringAfter stirring for several hours at that temperature
  6. temperaturethe mixture was cooled to 15 to 20° C.
  7. stirringcontinuously stirred for from 10 to 15 hours
  8. filtrationThe resulting deposit is filtrated
  9. washwashed with iced water
  10. customby drying

Sources & evidence

ORD record
ord-06a585752d7e467b80bb443690289d1c
Source dataset
uspto-grants-2006_06
Patent number
US07056959B2

Reaction notes

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