2-(Dimethylamino)acetyl chloride hydrochloride → 1-(3-Methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)-4-thiocyanatobenzene hydrochloride

HRID 258765Notes

Reaction equation

HRID 258765 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8][C:9]#[N:10])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]([NH:14][C:15]([O:17][CH3:18])=[O:16])=[S:13].Cl.[CH3:20][N:21]([CH3:26])[CH2:22][C:23]([Cl:25])=[O:24]>ClCCl>[ClH:25].[CH3:18][O:17][C:15]([NH:14][C:12](=[S:13])[NH:11][C:3]1[CH:4]=[CH:5][C:6]([S:8][C:9]#[N:10])=[CH:7][C:2]=1[NH:1][C:23](=[O:24])[CH2:22][N:21]([CH3:26])[CH3:20])=[O:16]

Participants

4

Reactant 2

HCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 214266632-Amino-1-(3-methoxycarbonyl-2-thioureido)-4-thiocyanatobenzene

Product 1

HCID 214266061-(3-Methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)-4-thiocyanatobenzene hydrochlorideYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 2-amino-1-(3-methoxycarbonyl-2-thioureido)-4-thiocyanatobenzene (5.6 g.) in dichloromethane (190 ml.) was treated in one portion at room temperature with N,N-dimethylglycyl chloride hydrochloride (3.82 g.). The stirring was continued for one hour and the mixture was allowed to stand overnight. The solid was filtered off and recrystallised from methanol to give 1-(3-methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)-4-thiocyanatobenzene hydrochloride (4.35 g.), m.p. 192°-193° C. (with decomposition).

Workup

  1. waitto stand overnight
  2. filtrationThe solid was filtered off
  3. customrecrystallised from methanol

Sources & evidence

ORD record
ord-48c2ac14960a4e8f80d31f2502127527
Source dataset
uspto-grants-1977_07
Patent number
US04034107

Reaction notes

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