Thionyl Chloride → 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonyl chloride hydrochloride

HRID 704240

Reaction equation

HRID 704240 reaction equation
S(Cl)([Cl:3])=O.[ClH:5].[N:6]1([CH2:11][CH:12]([N:14]2[C:27]3[CH:26]=[C:25]([C:28]([OH:30])=O)[CH:24]=[CH:23][C:22]=3[S:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH3:13])[CH2:10][CH2:9][CH2:8][CH2:7]1>C(Cl)Cl>[ClH:3].[N:6]1([CH2:11][CH:12]([N:14]2[C:27]3[CH:26]=[C:25]([C:28]([Cl:5])=[O:30])[CH:24]=[CH:23][C:22]=3[S:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH3:13])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1453664010-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride

Product 1

HCID 2007488610-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (12.7 cc) is added in the course of 5 minutes, with stirring at a temperature of 4° C., to a suspension of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride (9.77 g) in methylene chloride (250 cc), and stirring is continued for 90 minutes at a temperature of 20° C. The clear yellow solution obtained is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and dried to constant weight under reduced pressure (5 mm Hg; 0.67 kPa) at 50° C. to give 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonyl chloride hydrochloride (10.2 g) in the form of a yellow paste.

Workup

  1. customThe clear yellow solution obtained
  2. concentrationis concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  3. customdried to constant weight under reduced pressure (5 mm Hg; 0.67 kPa) at 50° C.

Sources & evidence

ORD record
ord-33461cce50594bfeb189316c444767a2
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Linked notes

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