HCID 15125464, compound → HCID 15125465, compound

HRID 2106749Notes

Reaction equation

HRID 2106749 reaction equation
CO[CH:3]([O:29][CH3:30])[CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)=[S:7]>C(O)=O>[CH3:30][O:29][CH:3]1[S:7][C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=4)[CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[N:5][CH2:4]1

Participants

3

Reactant 1

HCID 15125464HCID 15125464, compound

Product 1

HCID 15125465HCID 15125465, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 17.6 parts of N-(2,2-dimethoxyethyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thiourea and 120 parts of formic acid was stirred for 1 hour at room temperature. The reaction mixture was evaporated in vacuo and the residue was dissolved in 133 parts of dichloromethane. The mixture was neutralized with a sodium hydrogen carbonate solution. The precipitated product was filtered off, washed with water and dichloromethane and crystallized from 4-methyl-2-pentanone. The product was filtered off and dried, yielding 8.5 parts (52.0%) of 4,5-dihydro-5-methoxy-N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-thiazolamine; mp. 177.5° C. (int. 5).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in 133 parts of dichloromethane
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water and dichloromethane
  5. customcrystallized from 4-methyl-2-pentanone
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-92fd08de180948148b8d26226d532a9a
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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